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Journal articles on the topic 'Perylene bisimide (PBI)'

Author: Grafiati

Published: 5 June 2025

Last updated: 24 June 2025

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1

Ling, Cheng, Miao, Zhang, Zhang, and Zhu. "Synthesis and Photocontrolled Supramolecular Self-Assembly of Azobenzene-Functionalized Perylene Bisimide Derivatives." Polymers 11, no. 7 (2019): 1143. http://dx.doi.org/10.3390/polym11071143.

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Azobenzene (Azo) units were successfully introduced into perylene bisimide (PBI) structures in order to realize the photocontrolling of the morphology of the supramolecular assembly of PBI by a photoisomerization process. A total of three Azo-functionalized perylene bisimide derivatives (PBI1, PBI2, and PBI3) with different alkyl chain lengths were designed and synthesized by imidization of 3,4,9,10-perylene tetracarboxylic dianhydride with the corresponding amines. The structures of these compounds were characterized by proton nuclear magnetic resonance (1H NMR) and matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS). The photoisomerization behaviors of Azo units in PBIs were investigated using ultraviolet-visible (UV-VIS) absorption spectroscopy, which were obviously effected by solvents and the alkyl chain length. Furthermore, the photoisomerization of Azo units has the obviously regulatory effect on the morphology of supramolecular assembly of PBIs, especially for the medium-length alkyl chain-linked Azo-functionalized PBI derivative (PBI2). This research realized the photocontrolling of the morphology of the supramolecular assembly of PBI derivatives by photoisomerization of Azo units.

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2

Schmidt, Rüdiger, Peter Osswald, Martin Könemann, and Frank Würthner. "Synthetic Routes to Core-fluorinated Perylene Bisimide Dyes and their Properties." Zeitschrift für Naturforschung B 64, no. 6 (2009): 735–46. http://dx.doi.org/10.1515/znb-2009-0621.

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Numerous core-fluorinated perylene bisimide (PBI) dyes with various substituents at the imide positions have been synthesized by different methods. Core-difluorinated PBIs 4a-f are obtained by imidization of difluoro-substituted perylene bisanhydride 1 with appropriate primary amines or, alternatively, by nucleophilic halogen exchange reactions (Halex process) of the corresponding dibromosubstituted PBIs 2a-d,f with potassium fluoride. Core-tetrafluorinated PBIs 5a-c could also be synthesized by halogen exchange reactions of the respective tetrachlorinated PBIs 3a-c. In particular, core-fluorinated perylene bisimide pigments 4h, 5h containing hydrogen atoms in the imide positions could be obtained for the first time by deprotection of α-methylbenzyl-substituted precursors. Compared with core-unsubstituted perylene bisimides, these fluorinated dyes display hypsochromically shifted absorption and fluorescence spectra, and they exhibit fluorescence quantum yields up to unity, enabling bright yellow emission. The electrochemical properties of these electron-poor perylene bisimides have been studied. Furthermore, the packing features of a tetrafluorinated PBI derivative in the solid state have been discussed.

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3

Xu, Xu, Yuqi Li, Zhongqiang Xiong, et al. "Preparation and model of high-performance shape-memory polyurethane with hydroxylated perylene bisimide." RSC Advances 6, no. 111 (2016): 110329–36. http://dx.doi.org/10.1039/c6ra24393b.

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4

He, Xu, Bing Hu, Yan Yang, et al. "Synthesis, self-aggregation and cryopreservation effects of perylene bisimide–glycopeptide conjugates." Chemical Communications 57, no. 90 (2021): 12000–12003. http://dx.doi.org/10.1039/d1cc03835d.

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5

Ouyang, Guanghui, David Bialas, and Frank Würthner. "Reversible fluorescence modulation through the photoisomerization of an azobenzene-bridged perylene bisimide cyclophane." Organic Chemistry Frontiers 8, no. 7 (2021): 1424–30. http://dx.doi.org/10.1039/d0qo01635g.

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An azobenzene-bridged perylene bisimide cyclophane was designed and synthesized, which showed reversible fluorescence intensity switching under light-irradiation due to cooperative adjustments of PBI–PBI and PBI–Azo interactions.

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6

Lee, Ji-Eun, Ye Ri Han, Sujin Ham, Chul-Ho Jun, and Dongho Kim. "A solution-based single-molecule study of surface-bound PBIs: solvent-mediated environmental effects on molecular flexibility." Physical Chemistry Chemical Physics 19, no. 43 (2017): 29255–62. http://dx.doi.org/10.1039/c7cp04756h.

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7

Nastasi, Francesco, Giuseppina La Ganga, Sebastiano Campagna, et al. "Multichromophoric hybrid species made of perylene bisimide derivatives and Ru(ii) and Os(ii) polypyridine subunits." Physical Chemistry Chemical Physics 19, no. 21 (2017): 14055–65. http://dx.doi.org/10.1039/c7cp01597f.

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8

Mutoh, Katsuya, Michel Sliwa, Eduard Fron, Johan Hofkens, and Jiro Abe. "Fluorescence modulation by fast photochromism of a [2.2]paracyclophane-bridged imidazole dimer possessing a perylene bisimide moiety." Journal of Materials Chemistry C 6, no. 35 (2018): 9523–31. http://dx.doi.org/10.1039/c8tc02713g.

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9

Weißenstein, Annike, and Frank Würthner. "Metal ion templated self-assembly of crown ether functionalized perylene bisimide dyes." Chemical Communications 51, no. 16 (2015): 3415–18. http://dx.doi.org/10.1039/c4cc09443c.

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10

Al-Galiby, Qusiy, Iain Grace, Hatef Sadeghi та Colin J. Lambert. "Exploiting the extended π-system of perylene bisimide for label-free single-molecule sensing". Journal of Materials Chemistry C 3, № 9 (2015): 2101–6. http://dx.doi.org/10.1039/c4tc02897j.

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We demonstrate the potential of perylene bisimide (PBI) for label-free sensing of organic molecules by investigating the change in electronic properties of five symmetric and asymmetric PBI derivatives, which share a common backbone, but are functionalised with various bay-area substituents.

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11

Zheng, Jie, Jiawei Peng, Yu Xie, Yunze Long, Xin Ning, and Zhenggang Lan. "Study of the exciton dynamics in perylene bisimide (PBI) aggregates with symmetrical quasiclassical dynamics based on the Meyer–Miller mapping Hamiltonian." Physical Chemistry Chemical Physics 22, no. 32 (2020): 18192–204. http://dx.doi.org/10.1039/d0cp00648c.

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The exciton dynamics in one-dimensional stacked PBI (Perylene Bisimide) aggregates was studied with SQC-MM dynamics (Symmetrical Quasiclassical Dynamics based on the Meyer–Miller mapping Hamiltonian).

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12

Zhu, Mingguang, Yunxiang Chen, Xiaoyi Zhang, Meihui Chen, Hongyu Guo, and Fafu Yang. "Perylene bisimide with diphenylacrylonitrile on side-chain: strongly fluorescent liquid crystal with large pseudo Stokes shift based on AIE and FRET effect." Soft Matter 14, no. 32 (2018): 6737–44. http://dx.doi.org/10.1039/c8sm01183d.

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13

Aigner, D., R. I. Dmitriev, S. M. Borisov, D. B. Papkovsky, and I. Klimant. "pH-sensitive perylene bisimide probes for live cell fluorescence lifetime imaging." J. Mater. Chem. B 2, no. 39 (2014): 6792–801. http://dx.doi.org/10.1039/c4tb01006j.

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Several new perylene bisimide (PBI) probes comprising oligo-guanidine conjugates and cationic hydrogel nanoparticle structures were designed for sensing intracellular pH in live cell fluorescence lifetime imaging microscopy (FLIM).

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14

Solymosi, Iris, Swathi Krishna, Edurne Nuin, et al. "Diastereoselective formation of homochiral flexible perylene bisimide cyclophanes and their hybrids with fullerenes." Chemical Science 12, no. 47 (2021): 15491–502. http://dx.doi.org/10.1039/d1sc04242d.

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Perylene bisimide (PBI) cyclophanes linked by flexible malonates were functionalized with fullerenes. Modulation of the chemical environment enhances the chiral self-sorting, leading exclusively to the homochiral diastereomeric pair (M,M)/(P,P).

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15

Cao, Dapeng, Qifang Li, Manxi Zhou, Lei Zhu, Zhimin Sun, and Zhenqing Yang. "Tri-Petal Lilac-Like Perylene: Asymmetrical Substituted Platform for Regioselective Ether-Exchange Reaction." Synlett 28, no. 16 (2017): 2121–25. http://dx.doi.org/10.1055/s-0036-1590808.

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An asymmetrical tri-petal lilac-like platform based on perylene bisimide (PBI) was designed and synthesized to further perform the ether-exchange reaction, while common tetraphenoxy PBI analogue cannot do it. We found that the tri-petal lilac-like platform strategy not only avoids the regioisomers of difunctionalized PBI, but also is a precise and facile way to achieve regioselective introduction of alkyloxy, alkylthio and C=C double bond ended substituents onto the 1-position of perylene bay without the use and removal of the protecting groups. Due to the tunable photoelectrical properties and functional groups at bay position, these n-type PBI derivatives are promising materials for photovoltaic and supramolecular application.

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16

Karakostas, Nikolaos, Antonia Kaloudi-Chantzea, Elisabeth Martinou, et al. "Energy transfer within self-assembled cyclic multichromophoric arrays based on orthogonally arranged donor–acceptor building blocks." Faraday Discussions 185 (2015): 433–54. http://dx.doi.org/10.1039/c5fd00083a.

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We herein present the coordination-driven supramolecular synthesis and photophysics of a [4+4] and a [2+2] assembly, built up by alternately collocated donor–acceptor chromophoric building blocks based, respectively, on the boron dipyrromethane (Bodipy) and perylene bisimide dye (PBI). In these multichromophoric scaffolds, the intensely absorbing/emitting dipoles of the Bodipy subunit are, by construction, cyclically arranged at the corners and aligned perpendicular to the plane formed by the closed polygonal chain comprising the PBI units. Steady-state and fs time-resolved spectroscopy reveal the presence of efficient energy transfer from the vertices (Bodipys) to the edges (PBIs) of the polygons. Fast excitation energy hopping – leading to a rapid excited state equilibrium among the low energy perylene-bisimide chromophores – is revealed by fluorescence anisotropy decays. The dynamics of electronic excitation energy hopping between the PBI subunits was approximated on the basis of a theoretical model within the framework of Förster energy transfer theory. All energy-transfer processes are quantitatively describable with Förster theory. The influence of structural deformations and orientational fluctuations of the dipoles in certain kinetic schemes is discussed.

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17

Kaur, Sandeep, Manoj Kumar, and Vandana Bhalla. "Supramolecular ensemble of PBI derivative and copper nanoparticles: a light harvesting antenna for photocatalytic C(sp2)–H functionalization." Green Chemistry 18, no. 21 (2016): 5870–83. http://dx.doi.org/10.1039/c6gc01728b.

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A supramolecular ensemble of triazole-appended perylene bisimide (PBI) derivative 4 and in situ generated copper nanoparticles (CuNPs) serves as a light-harvesting antenna in photocatalytic C(sp<sup>2</sup>)–H alkynylation and amination reactions of arenes under mild and eco-friendly conditions.

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18

Ma, Weitao, Leiqiang Qin, Yu Gao, et al. "A perylene bisimide network for high-performance n-type electrochromism." Chemical Communications 52, no. 93 (2016): 13600–13603. http://dx.doi.org/10.1039/c6cc07962h.

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A micro-porous network thin film of core-tetrachlorinated perylene bisimide (PBI) was deposited by electrochemical polymerization, which showed reversible n-doping/dedoping processes at rather low potentials, accompanied by color changes from an orange red (neutral) state to a transparent (radical anion) state and further to an aquamarine (dianion) state.

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19

Sarbu, Alexandru, Laure Biniek, Jean-Michel Guenet, Philippe J. Mésini, and Martin Brinkmann. "Reversible J- to H-aggregate transformation in thin films of a perylenebisimide organogelator." Journal of Materials Chemistry C 3, no. 6 (2015): 1235–42. http://dx.doi.org/10.1039/c4tc02444c.

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A perylene bisimide organogelator is shown to behave as a reversible stimuli responsive material: thermal annealing and contact with organic non solvents allow to switch back and forth between a green J-type (Form I) and a red H-type (Form II) aggregate in thin films and powders of a N,N′-substituted H-bonding perylenebisimide (PBI-C10).

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20

Zhang, Wenqiang, Shu Zhong, Li Nian, et al. "Perylene bisimide as the cathode modifier in organic photovoltaics: the role of aggregation morphology on the interlayer performance." RSC Advances 5, no. 50 (2015): 39973–77. http://dx.doi.org/10.1039/c5ra03988f.

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Nanorods and nanoparticles of perylene bisimides (PBI-1) were prepared and applied as cathode interlayer in organic photovoltaic devices. The device performance showed important relation with the morphology of the interlayer.

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21

Wang, Ying, Xinguo Yang, Siyu Li, Tao Long, and Wei Li. "Organic Acid Regulated Self-Assembly and Photophysical Properties of Perylene Bisimide Derivatives." Materials 13, no. 7 (2020): 1656. http://dx.doi.org/10.3390/ma13071656.

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In this work, perylene bisimide derivatives (PBI-1 and PBI-2) with tertiary amine groups were designed and synthesized. To control the final morphologies and properties of their aggregates, seven kinds of organic acids were used to alter the self-assembly environment. The influence of organic acids on the morphology of the aggregates was investigated. Photophysical properties of the aggregates were markedly affected by the kind and concentration of the organic acid. The thermal and gas sensitivities of the PBI-1 aggregates were studied with the use of UV–visible spectroscopy and digital imaging. The shift of the UV–visible spectra varied with time, temperature, acid type and acid concentration. Furthermore, PBI-1 aggregates showed a red-to-blue color change after addition of seven organic acids, whereas the color of the PBI-2 aggregates remained red. These changes of morphologies, photophysical properties and their thermal and gas sensitivities make these aggregates potentially useful in the fields of optoelectronics or sensors.

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22

Zhang, Xiaoxiao, Tingyuan Gong, Hong Chi, and Tianduo Li. "Nanostructured polyurethane perylene bisimide ester assemblies with tuneable morphology and enhanced stability." Royal Society Open Science 5, no. 3 (2018): 171686. http://dx.doi.org/10.1098/rsos.171686.

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Size control has been successfully achieved in inorganic materials, but it remains a challenge in polymer nanomaterials due to their polydispersity. Here, we report a facile approach to tailor the diameters of polyurethane (PU) nanoparticles (490 nm, 820 nm and 2.1 µm) via perylene bisimide (PBI) assisted self-assembly. The formed morphologies such as spindle, spherical and core–shell structures depend on the ratio of PBI and polymer concentrations. It is shown that the formation of PU nanoparticles is directed by π–π stacking of PBI and the morphology transition is not only affected by the amount of PBI incorporated, but also influenced by solvent, which controls the initial evaporation balance. Furthermore, the prepared PUs exhibit retained optical stability and enhanced thermal stability. The PUs, designed to have conjugated PBI segments in backbones, were synthesized via ring-opening and condensation reactions. Compared with the neat PU, gel permeation chromatography shows narrower molecular weight distribution. Fluorescence spectra and ultraviolet–visible spectra indicate retained maximum emission wavelength of PBI at 574 nm and 5.2% quantum yields. Thermo-gravimetric analysis and differential scanning calorimetry reveal 79°C higher decomposition temperature and 22°C higher glass transition temperature. This study provides a new way to fabricate well-defined nanostructures of functionalized PUs.

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23

Marcia, Mario, Prabhpreet Singh, Frank Hauke, Michele Maggini, and Andreas Hirsch. "Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit." Org. Biomol. Chem. 12, no. 36 (2014): 7045–58. http://dx.doi.org/10.1039/c4ob01007h.

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24

Tsutsumi, Naoto, Takafumi Sassa, Tam Van Nguyen, et al. "Photoconductive Dynamics of Photorefractive Poly((4-Diphenylamino)benzyl Acrylate)-Based Composites Sensitized by Perylene Bisimide." Polymers 17, no. 1 (2025): 96. https://doi.org/10.3390/polym17010096.

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The transient dynamics of photocurrents for poly((4-diphenylamino)benzyl acrylate) (PDAA)-based photorefractive (PR) polymers sensitized with perylene bisimide derivative N,N′-diisopropylphenyl-1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxyl bisimide (PBI) at various composition ratios were studied. The PR polymer included (4-(diphenylamino)phenyl)methanol (TPAOH) photoconductive plasticizer and (4-(azepan-1-yl)-benzylidene) malononitrile nonlinear optical dye as well, which are needed for inducing PR effects. All the photocurrents measured at 640 nm were well simulated by a two-trapping site model considering photocarrier generation and recombination processes of the charge transfer (CT) complex between PBI and PDAA. The process of photocurrent simulation allowed for analyses of the dependences of hole mobility, quantum efficiency (QE) of photocarrier generation, trapping parameters, and recombination coefficient on the PDAA/TPAOH content. Finally, the PDAA content dependences of the trapping and recombination properties were compared with those of the PR parameters of the optical diffraction efficiency, optical gain, and response time.

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25

Wei, Kang, Haitao Zhang, Jianbo Qu, Jianyong Wang, Yang Bai, and Futao Sai. "Recyclable Shape-Memory Waterborne Polyurethane Films Based on Perylene Bisimide Modified Polycaprolactone Diol." Polymers 13, no. 11 (2021): 1755. http://dx.doi.org/10.3390/polym13111755.

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Currently, much attention is given to the functionality and recyclability of waterborne polyurethane (WPU). Herein, ε-caprolactone was used as a chain extender for grafting onto perylene bisimide (PBI) and 1,4-butanediol (BDO) via ring-opening reactions to obtain PBI-PCL and BDO- PCL. Then, two kinds of WPU, namely PBI-WPU (PWPU) and BDO-WPU (BWPU), were fabricated using PBI-PCL/polytetrahydrofuran ether glycol (PTMG) and BDO-PCL/PTMG, respectively, as mixed soft segments. The properties and appearance of PWPU and BWPU emulsions were analyzed in terms of particle size, zeta potential and TEM images, and the results showed that PWPU emulsions had uniform particle size distribution and decent storage stability. AFM and DMA results revealed that PWPU films possessed a more significant degree of microphase separation and a higher glass transition temperature (Tg) than BWPU films. The PWPU films displayed good shape-memory and mechanical properties, with tensile strength up to 58.25 MPa and elongation at break up to 1241.36%. TGA analysis indicated that PWPU films had better thermal stability than BWPU films. More importantly, the PWPU films could be dissolved in a mixed solvent of acetone/ethanol (v/v = 2:1) at room temperature. The dissolved PWPU could be dispersed in deionized water to prepare waterborne polyurethane again. After the recycling process was repeated three times, the recycled PWPU emulsion still exhibited good storage stability. The recycled PWPU films maintained their original thermal and mechanical properties. Comparing the properties of BWPU and PWPU showed that the soft segment structure had important influence on waterborne polyurethane performance. Therefore, PWPU may have great potential applications in making recycling and shape-memory coating or paint.

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26

Maier, Johannes, Martti Pärs, Tina Weller, Mukundan Thelakkat, and Jürgen Köhler. "Switching or blinking? – The switching behaviour of single photochromic triads." EPJ Web of Conferences 190 (2018): 04014. http://dx.doi.org/10.1051/epjconf/201819004014.

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Photochromic molecules can be interconverted between two bistable conformations by light [1–3]. Irie and coworkers described a strategy to achieve superior fluorescence characteristics and outstanding switching characteristics of a photochromic unit by linking strong fluorophores covalently to photochromic building blocks [3,4]. Accordingly, we synthesised molecular triads that consist of two perylene bisimide (PBI) fluorophores covalently linked to a dithienylcyclopentene (DCP) photochromic switch, see fig. 1. Such kinds of triads are promising candidates for super-resolution microscopy like RESOLFT and PALM [5,6], or can be used as optical transistors or memories [4,7].

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27

Seifert, Sabine, David Schmidt, and Frank Würthner. "An ambient stable core-substituted perylene bisimide dianion: isolation and single crystal structure analysis." Chemical Science 6, no. 3 (2015): 1663–67. http://dx.doi.org/10.1039/c4sc03671a.

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28

Rühe, Jessica, David Bialas, Peter Spenst, Ana-Maria Krause, and Frank Würthner. "Perylene Bisimide Cyclophanes: Structure–Property Relationships upon Variation of the Cavity Size." Organic Materials 02, no. 02 (2020): 149–58. http://dx.doi.org/10.1055/s-0040-1709998.

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Five cyclophanes composed of two perylene bisimide (PBI) dyes and various CH2–arylene–CH2 linker units were synthesized. PM6-D3H4 geometry-optimized structures and a single crystal for one of these cyclophanes reveal well-defined distances between the two coplanar PBI units in these cyclophanes, spanning the range from 5.0 to 12.5 Å. UV/vis absorption spectra reveal a redistribution of oscillator strength of the vibronic bands due to a H-type exciton coupling even for the cyclophane with the largest interchromophoric distance. A quantitative evaluation according to the Kasha–Spano theory affords exciton coupling strengths ranging from 64 cm−1 for the largest cyclophane up to 333 cm−1 for the smallest one and a surprisingly good fit to the cubic interchromophoric distance in the framework of the point-dipole approximation. Interchromophoric interaction is also noticed in fluorescence lifetimes that are significantly increased for all five cyclophanes as expected for H-coupled chromophores due to a decrease of the radiative rate. For the three largest cyclophanes with interchromophoric distances of >9 Å, fluorescence quantum yields remain high in chloroform (>88%), whilst for the smaller ones with interchromophoric distances <6 Å, additional nonradiative pathways lead to a pronounced fluorescence quenching.

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29

Wang, Gang, Xingmao Chang, Junxia Peng, et al. "Towards a new FRET system via combination of pyrene and perylene bisimide: synthesis, self-assembly and fluorescence behavior." Physical Chemistry Chemical Physics 17, no. 7 (2015): 5441–49. http://dx.doi.org/10.1039/c4cp04860a.

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30

Alloa, Elisa, Vincenzo Grande, Rishat Dilmurat, David Beljonne, Frank Würthner, and Sophia C. Hayes. "Resonance Raman study of the J-type aggregation process of a water soluble perylene bisimide." Physical Chemistry Chemical Physics 21, no. 33 (2019): 18300–18309. http://dx.doi.org/10.1039/c9cp01874c.

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31

Zhang, Jinling, Ke Liu, Gang Wang, et al. "Detection of gaseous amines with a fluorescent film based on a perylene bisimide-functionalized copolymer." New Journal of Chemistry 42, no. 15 (2018): 12737–44. http://dx.doi.org/10.1039/c8nj02540a.

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32

Tilmann, Rita, Corinna Weiß, Conor P. Cullen, et al. "Highly Selective Non-Covalent On-Chip Functionalization of Layered Materials." Advanced Electronics Materials 7 (January 15, 2021): 2000564. https://doi.org/10.1002/aelm.202000564.

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Non-covalent functionalization of layered 2D materials is an essential tool to modify and fully harness their optical, electrical, and chemical properties. Herein, a facile method enabling the selective formation of self-assembled monolayers (SAMs) of perylene bisimide (PBI) on transition metal dichal- cogenides (TMDs), directly on the growth substrate (on-chip), is presented. Laterally-resolved infrared atomic force microscopy (AFM-IR) and time-of- flight secondary ion mass spectrometry (TOF-SIMS) are applied as superior techniques to gain detailed information beyond traditional surface analysis techniques, such as Raman spectroscopy and AFM, on TMD/PBI structures. The highly selective functionalization conducted in organic solution on MoS2 and WSe2 opens up a pathway to controllable, versatile functionalization of layered materials, which is highly sought after for its potential in passiva- tion, tuning of properties and applications in optics, electronics, and (bio-) sensing.

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33

Cui, Lingyun, Yang Jiao, Anhe Wang, et al. "Regulating morphologies and near-infrared photothermal conversion of perylene bisimide via sequence-dependent peptide self-assembly." Chemical Communications 54, no. 18 (2018): 2208–11. http://dx.doi.org/10.1039/c8cc00177d.

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The behavior of PBI self-assembly can be precisely organised by the conjugation of sequence dependent dipeptides in aqueous media resulting in different assembled nanostructures with improved radical anions yield and enhanced photothermal conversion efficiency.

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34

Kaur, Sandeep, Manoj Kumar, and Vandana Bhalla. "Aggregates of perylene bisimide stabilized superparamagnetic Fe3O4nanoparticles: an efficient catalyst for the preparation of propargylamines and quinolines via C–H activation." Chemical Communications 51, no. 91 (2015): 16327–30. http://dx.doi.org/10.1039/c5cc05752c.

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Supramolecular aggregates of the PBI derivative3serve as reactors and stabilizers for the preparation of Fe<sub>3</sub>O<sub>4</sub>nanoparticles, which exhibit high catalytic efficiency for the preparation of propargylamines and quinolines derivativesviaC–H activation.

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35

Sarbu, Alexandru, Patrick Hermet, David Maurin, et al. "Supramolecular organization of a H-bonded perylene bisimide organogelator determined by transmission electron microscopy, grazing incidence X-ray diffraction and polarized infra-red spectroscopy." Physical Chemistry Chemical Physics 19, no. 48 (2017): 32514–25. http://dx.doi.org/10.1039/c7cp06761e.

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36

Martínez, Manuel A., Elisa E. Greciano, Jorge Cuéllar, José M. Valpuesta, and Luis Sánchez. "Globular Aggregates Stemming from the Self-Assembly of an Amphiphilic N-Annulated Perylene Bisimide in Aqueous Media." Nanomaterials 11, no. 6 (2021): 1457. http://dx.doi.org/10.3390/nano11061457.

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Herein, we describe the synthesis of highly emissive amphiphilic N-annulated PBI 1 decorated with oligo ethylene glycol (OEG) side chains. These polar side chains allow the straightforward solubility of 1 in solvents of different polarity such as water, iPrOH, dioxane, or chloroform. Compound 1 self-assembles in aqueous media by π-stacking of the aromatic units and van der Waals interactions, favored by the hydrophobic effect. The hypo- and hypsochromic effect observed in the UV-Vis spectra of 1 in water in comparison to chloroform is diagnostic of H-type aggregation. Solvent denaturation experiments allow deriving the free Gibbs energy for the self-assembly process in aqueous media and the factor m that is indicative of the influence exerted by a good solvent in the stability of the final aggregates. The ability of compound 1 to self-assemble in water yields globular aggregates that have been visualized by TEM imaging.

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37

Yang, Gui-Xia, Hai-Lin Fan, Xiao-Di Niu, and Zong-Hao Huang. "A theoretical study of bipolar organic transport material: Disilanyl double-pillared bisanthracene (SiDPBA)." Canadian Journal of Chemistry 89, no. 10 (2011): 1257–63. http://dx.doi.org/10.1139/v11-085.

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A novel anthracene derivative, disilanyl double-pillared bisanthracene (SiDPBA), has been recently synthesized, which effectively functions as a bipolar carrier transport material in OLEDs. Its charge transport properties have been systemically investigated by band model and hopping model. Band structure calculations of SiDPBA show that the dispersions of the larger valence band and conduction band are comparable, which demonstrates that both electron and hole are favoured for transport, and that SiDPBA has the potential to be used as bipolar transport material from the viewpoint of band model. The density of states and transfer integrals in the main pathways show that it is the edge-to-face CH···π interaction that determines the charge transport property, and that the SiMe2 group contibutes little to it. The calculated charge mobilities of holes and electrons are 0.461 and 0.116 cm2·V–1·s–1, respectively. They are the same order of magnitude, and the electron mobility is on the order of magnitude of perylene-3,4:9,10-tetracarboxylic acid bisimide (PBI) derivatives (0.34 cm2·V–1·s–1). Both models demonstrate that ·SiDPBA has the potential to be used as a bipolar transport material.

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Nowak-Król, Agnieszka, Benjamin Fimmel, Minjung Son, Dongho Kim, and Frank Würthner. "Photoinduced electron transfer (PET) versus excimer formation in supramolecular p/n-heterojunctions of perylene bisimide dyes and implications for organic photovoltaics." Faraday Discussions 185 (2015): 507–27. http://dx.doi.org/10.1039/c5fd00052a.

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Foldamer systems comprised of two perylene bisimide (PBI) dyes attached to the conjugated backbones of 1,2-bis(phenylethynyl)benzene and phenylethynyl-bis(phenylene)indane, respectively, were synthesized and investigated with regard to their solvent-dependent properties. UV/Vis absorption and steady-state fluorescence spectra show that both foldamers exist predominantly in a folded H-aggregated state consisting of π–π-stacked PBIs in THF and in more random conformations with weaker excitonic coupling between the PBIs in chloroform. Time-resolved fluorescence spectroscopy and transient absorption spectroscopy reveal entirely different relaxation pathways for the photoexcited molecules in the given solvents, i.e. photoinduced electron transfer leading to charge separated states for the open conformations (in chloroform) and relaxation into excimer states with red-shifted emission for the stacked conformations (in THF). Supported by redox data from cyclic voltammetry and Rehm–Weller analysis we could relate the processes occurring in these solution-phase model systems to the elementary processes in organic solar cells. Accordingly, only if relaxation pathways such as excimer formation are strictly avoided in molecular semiconductor materials, excitons may diffuse over larger distances to the heterojunction interface and produce photocurrent via the formation of electron/hole pairs by photoinduced electron transfer.

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39

Sharma, G. D., M. S. Roy, J. A. Mikroyannidis, and K. R. Justin Thomas. "Synthesis and characterization of a new perylene bisimide (PBI) derivative and its application as electron acceptor for bulk heterojunction polymer solar cells." Organic Electronics 13, no. 12 (2012): 3118–29. http://dx.doi.org/10.1016/j.orgel.2012.07.002.

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40

Hiroto, Satoru, та Mana Wakita. "Supramolecular Assembly of Nitrogen-Containing Curved π-Conjugated Molecules to Polar Crystal". ECS Meeting Abstracts MA2024-01, № 14 (2024): 1145. http://dx.doi.org/10.1149/ma2024-01141145mtgabs.

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The chemistry of curved π-conjugated molecules has been extensively studied because of the development of their synthetic approach. Among the numerous studies, we have been engaged in nitrogen-containing curved π-conjugated molecules. These molecules have extended optical properties, redox-active behaviors, and electron-donating ability due to the electron-rich nature of nitrogen atoms. Recently, we have focused on the supramolecular assembling behavior of these compounds. For example, we have reported buckycatcher consisted of two azabuckybowls, providing two-photon absorbing host-guest complexes with fullerenes. In this presentation, we would like to show the packing behavior using π-extended azahelicenes and azabuckybowls. Our group has developed π-extended aza[5]helicene derivatives, showing brilliant emissive features. Recently, we succeeded in the synthesis of unsymmetrically substituted azahelicenes. We found that their stackings in the crystal were dependent on the substituent. X-ray diffraction analysis for all products showed π-stacked conformation with each other in the crystal (Figure 1b). In particular, azahelicenes with triisopropylsilyl groupswere found to align their dipole moments to form a one-dimensional columnar structure in the crystal. Polar crystals are expected to have applications in ferroelectric, piezoelectric, and nonlinear optical response materials. This is the first example of a polar crystal with helicenes, paving the way for novel piezoelectric organic materials. The second topic is related to azabuckybowl. In the crystal, azabuckybowl forms a face-to-face dimer by concave-convex interaction. In this study, we prepared two types of azabuckybowl perylene bisimide (PBI) dyads connected with alkyne linkages. PBIs have also been reported to show columnar stacking in solution. We anticipated that the segregate stacking should be achieved by recognizing the difference in structures between the bowl and planar geometry. The UV/vis absorption spectra revealed the presence of intramolecular charge-transfer interaction. In addition, the concentration-dependent absorption spectra and 1H NMR spectra indicated PBI and azabuckybowl units stacked with each other independently in solution (Figure 1a). Here, we would like to discuss about the effect of the effect of molecular shape on the supramolecular assembly with the data obtained using these compounds. Figure 1

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41

Meenal, Kataria, Kumar Manoj, and Bhalla Vandana. "Smart fluorescent supramolecular assemblies: Self-assembly in the presence of metal ions and anions in mixed aqueous media." Journal of India Chemical Society Vol. 95, Dec 2018 (2018): 1559–77. https://doi.org/10.5281/zenodo.5644786.

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Department of Chemistry, UGC Sponsored Centre for Advanced Studies-II, Guru Nanak Dev University, Amritsar-143 005, Punjab, India <em>E-mail</em>: vanmanan@yahoo.co.in <em>Manuscript received online 25 November 2018, accepted 29 November 2018</em> Recently, aggregation induced emission (AIE) phenomena has been extensively explored for preparation of fluorescent assemblies which find wide spread applications in diverse fields such as molecular recognition, catalysis, sensing and fabrication of optoelectronic devices. The fluorescent assemblies having specific binding sites act as selective sensory ensembles for the detection of various biologically important metal ions and anions such as Na<sup>+</sup>, K<sup>+</sup>, Mg<sup>2+</sup>, Ca<sup>2+</sup>, Fe<sup>2+</sup>, Zn<sup>2+</sup>, SO<sub>4</sub><sup>2–</sup>, NO<sub>3 </sub>C<sub>2</sub>O<sub>4</sub><sup>2</sup>– and CH<sub>3</sub>COO<sup>–</sup> ions. In some cases these fluorescent aggregates further undergo metal ion or anion induced aggregation or disaggregation in mixed aqueous media which results in modulation of their self-assembled architectures. The present review focuses on the summarization of different findings highlighting the concepts of AIEE for the preparation of fluorescent materials and their application for the development of ion coordinated self-assembled architectures.

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Lundy, Ross, Emily R. Draper, and James J. Walsh. "Amino acid appended perylene bisimides: self-assembly, immobilization on nanocrystalline TiO2, and electrochromic properties." New Journal of Chemistry 42, no. 23 (2018): 19020–25. http://dx.doi.org/10.1039/c8nj04214d.

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Titanium dioxide (TiO<sub>2</sub>) nanoparticle films have been used as a conducting support for the immobilisation of alanine-appended perylene bisimides (PBI-A) via dip-coating and carboxylate chemisorption.

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Wang, Yi Jia, Zeyu Li, Jiaqi Tong, et al. "The fluorescence properties and aggregation behavior of tetraphenylethene–perylenebisimide dyads." Journal of Materials Chemistry C 3, no. 15 (2015): 3559–68. http://dx.doi.org/10.1039/c4tc02550d.

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Perylene-bisimides (PBIs) modified with tetraphenylethene (TPE) at N-terms show unique X-aggregation and are non-fluorescent in solution, aggregate and solid film due to the photoinduced charge transfer between TPE and PBI subunits.

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44

Qi, Rui, Xiaotian Huang, Ting Yang, et al. "Morphology Control and Spectral Study of the 2D and Hierarchical Nanostructures Self-Assembled by the Chiral Alanine-Decorated Perylene Bisimides." Molecules 29, no. 19 (2024): 4610. http://dx.doi.org/10.3390/molecules29194610.

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Tailoring the morphologies and optical properties of the 2D and hierarchical nanostructures self-assembled by the π-conjugated molecules is both interesting and challenging. Herein, a series of 2D ribbon-like nanostructures with single or multiple H-aggregated perylene bisimides (PBI) monolayer and hierarchical nanostructures (including straw-like, dumbbell-shaped, and rod-like nanostructures) are fabricated by solution self-assembly of three chiral alanine-decorated PBI. The influence of the solvent’s dissolving capacity, the chirality of alanine, and the preparation methods on the morphologies and optical properties of the nanostructures were extensively studied. It was observed that the hierarchical nanostructures are formed by the reorganization of the 2D ribbon-like nanostructures. The size of the 2D ribbon-like nanostructures and the amount of the hierarchical nanostructures increase with the decrease in the solvent’s dissolving capacity. The small chiral alanine moiety is unable to induce chirality in the nanostructures, owing to its low steric hindrance and the dominant strong π-π stacking interaction of the PBI skeleton. A weaker π-π stacking interaction and better H-aggregated arrangement of the PBI skeleton could reduce the low-wavelength fluorescence intensity. The process of heating, cooling, and aging promotes the formation of H-aggregation in the PBI skeleton. The region of spectral overlap of the PBI solutions increases with the decrease in the dissolving capacity of the solvent and the steric hindrance of the chiral alanine. This study supplies a view to tailor the morphologies and optical properties of the nanostructures, which could be used as sensors and photocatalysts.

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Maier, Johannes, Martti Pärs, Katja Gräf, Mukundan Thelakkat, and Jürgen Köhler. "Light controls light: single molecules as optical switches." EPJ Web of Conferences 190 (2018): 02006. http://dx.doi.org/10.1051/epjconf/201819002006.

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In recent years much attention has been given to design multistate molecular components with functionalities that cover the range from simple switches to logic gates [1-3]. In this regard photochromic molecules, i.e., molecules that can be interconverted between two bistable forms by light, have played an important role. Promising candidates that fulfill obvious demands such as high photochemical/ photophysical stability and high fatigue resistance are compounds of the family of diarylethenes [2,3]. However, a serious drawback of this class of molecules is a low fluorescence quantum yield. Therefore we adapted the strategy developed by Irie and coworkers [2,3], to chemically synthesize complex tailor-made triads consisting of a photochromic dithienylcyclopentene (DCP) unit covalently linked to two peryline bisimide (PBI) molecules that are known as strong fluorophores, see fig.1 inset top left. This facilitates the combination of high fatigue resistance and high fluorescence quantum yield. Illumination with light in the UV spectral region induces a ring-closure reaction of the DCP and leads to a state with suppressed fluorescence from the PBIs, whereas light in the VIS spectral region yields a ring opening reaction of the DCP and restores the fluorescence from the PBI units. This allowed us to verify functionalities like optical gating and amplifying, yet where the electrons have been replaced by photons as signal carriers [4-6], see fig.1.

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46

Banerjee, Arindam, Purnadas Ghosh, Soumyajit Hazra, Kousik Gayen, Niladri Hazra, and Arun K. Nandi. "Peptide appended perylene bisimide containing silver nanoparticle-based trihybrid system with GO: improvement of photocatalytic and photo-switching behaviour." New Journal of Chemistry, 2024. http://dx.doi.org/10.1039/d3nj05662g.

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This report demonstrates a facile environmentally friendly synthesis of a trihybrid system (PBI-NP-GO) consisting of perylene bisimide appended peptide (PBI-UW) nanofibers, silver nanoparticles (PBI-AgNP) and graphene oxide (GO) nano-sheet. The...

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47

Paulino, Victor, Kaixuan Liu, Valentino Cesiliano та ін. "Covalent post-assembly modification of π-conjugated supramolecular polymers delivers structurally robust light-harvesting nanoscale objects". Nanoscale, 2023. http://dx.doi.org/10.1039/d2nr06806k.

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48

Nagler, Oliver, Kazutaka Shoyama, Olga Anhalt, et al. "Boron-, Carbon-, and Silicon-Bridged 1,12-Dihydroxy-Perylene Bisimides with Tuned Structural and Optical Properties." Organic Chemistry Frontiers, 2023. http://dx.doi.org/10.1039/d3qo01389h.

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Establishing suitable design strategies to tailor the functional properties of perylene bisimide (PBI) dyes are critical for their successful application in various devices. Herein, we report a new synthetic strategy...

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49

Berruyer, Valentine Le, Aurelie Perrier, and Mayeul Collot. "Photoconvertible and Photoactivatable Perylene BisImide Based on Photocyclization." Advanced Optical Materials, September 24, 2024. http://dx.doi.org/10.1002/adom.202401511.

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AbstractPhotomodulable fluorophores constitute advanced materials as they possess the ability to modify their photophysical properties upon photoirradiation. A new mechanism of photoconversion is recently established, called Directed Photooxidation Induced Conversion based on the coupling of fluorophores with Aromatic Singlet oxygen Reactive Moieties (ASORMs). In this work, The Directed Photooxidation Induced Conversion (DPIC) mechanism is intended to be applied to Perylene BisImide (PBI) due to its appealing photophysical properties. The experimental results showed that coupling two ASORMs to the PBI core, here furan and pyrrole, led to impressive photomodulable fluorophores. While PBI‐F exhibited a photoconversion of 100 nm shift, PBI‐P displayed an 80‐fold fluorescence intensity enhancement upon photoactivation. Analysis of the photoproducts showed that the conversion do not involve an addition of singlet oxygen on the ASORM. Instead, photoconversion occurred through efficient successive photocyclizations. Finally, intracellular vesicles are successfully photoconverted by means of endocytosed PLGA‐polymer nanoparticles loaded with PBI‐F. This study highlights the unique capability of furan‐ and pyrrole‐conjugated fluorophores to enable advanced optical materials with phototransformation properties.

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Weh, Manuel, Asja A. Kroeger, Olga Anhalt, Amir Karton, and Frank Wuerthner. "Mutual Induced Fit Transition Structure Stabilization of Corannulene’s Bowl-to-Bowl Inversion in a Perylene Bisimide Cyclophane." Chemical Science, 2023. http://dx.doi.org/10.1039/d3sc05341e.

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