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Journal articles on the topic 'Pyrrolic dyes'

Author: Grafiati

Published: 24 April 2022

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1

Sternberg, E., and D. Dolphin. "Pyrrolic Photosensitizers." Current Medicinal Chemistry 3, no. 4 (August 1996): 239–72. http://dx.doi.org/10.2174/092986730304220302110921.

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Abstract: There are three major classes of photosensitizers which can initiate a phototoxic effect to tissues upon irradiation. These are the cationic dyes (Type I Photosensitizer), the psoralens (Type I and II Photosensitizer), and cyclic polypyrrolic compounds (Type II Photosensitizer). The polypyrrolic compounds such as porphyrins have been investigated since the late 1800's for their ability to destroy tissue. In the last ten years, compounds such as chlorins and expanded porphyrins have begun to dominate the preclinical field because they can be activated with light at wavelengths tissue does not effectively absorb. The results of these investigation have been reported in more than 10,000 papers in the field covering aspects from mechanisms of action, photophysics, structure activity relationships, new compound development and clinical investigations. With the approval of PHOTOFRJN®, (porfimer sodium), the first of the pyrrolic compounds to win acceptance by international regulatory bodies and with nearly 10 other second generation compounds undergoing early clinical trials for diseases ranging from esophageal and skin cancers to age related macular degeneration, the field of photodynamic therapy would seem to have a bright future.

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2

Zhang, Chen, and Kenneth S. Suslick. "Syntheses of boronic-acid-appended metalloporphyrins as potential colorimetric sensors for sugars and carbohydrates." Journal of Porphyrins and Phthalocyanines 09, no. 09 (September 2005): 659–66. http://dx.doi.org/10.1142/s1088424605000770.

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Boronic-acid-based dyes have been widely studied in the past decade as potential sensors for sugars and carbohydrates, owing to the strong interaction of boronic acid and diols. In this work, two boronic-acid-appended metalloporphyrins were synthesized by new routes and tested as potential sugar and carbohydrate sensors. Boronic acid substituents were attached either to a β-pyrrolic position ((2-dihydroxylboryl-5,10,15,20-tetraphenylporphyrinato)zinc(II), 1) or to the meso-position ((10-dihydroxylboryl-5,15-diphenylporphyrinato)zinc(II), 2) of the porphyrin core. These complexes were tested as potential carbohydrate sensors; unfortunately, no UV-vis or fluorescence spectra changes were observed with the addition of glucose or fructose. Molecular orbital calculations confirm little electronic conjugation between the porphyrin π-system and the boronic acid substituents in either pyrrolic or meso-positions.

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3

E, Lei, Wei Li, Jiaming Sun, Zhenwei Wu, and Shouxin Liu. "N-Doped Carbon Aerogels Obtained from APMP Fiber Aerogels Saturated with Rhodamine Dye and Their Application as Supercapacitor Electrodes." Applied Sciences 9, no. 4 (February 13, 2019): 618. http://dx.doi.org/10.3390/app9040618.

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We developed an efficient and environmentally friendly strategy for synthesizing an N-doped carbon aerogel by the carbonization of an alkaline peroxide mechanical pulp (APMP) fiber aerogel saturated with rhodamine B (RB) dyes. The APMP aerogel was prepared via cellulose extraction, sol-gel, and freeze drying. The resulting aerogel had a high adsorption capacity (250 mg g−1) and a fast adsorption rate (within 30 s) towards RB dyes. The saturated aerogel was used as a starting material for further carbonization to prepare N-doped carbon aerogels. SEM studies showed that the 3D network structure of the APMP aerogels was well preserved after RB adsorption and carbonization. The prepared carbon aerogel exhibited a graphitized structure, and N (2.15%) was doped at pyridinic N and pyrrolic N sites in the 3D carbon network. The specific capacitance of the N-doped carbon aerogel reached 185 F g−1 at a current density of 1 A g−1, which is higher than carbon aerogels (155 F g−1).

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4

Beverina, Luca, Martin Drees, Antonio Facchetti, Matteo Salamone, Riccardo Ruffo, and Giorgio A. Pagani. "Bulk Heterojunction Solar Cells - Tuning of the HOMO and LUMO Energy Levels of Pyrrolic Squaraine Dyes." European Journal of Organic Chemistry 2011, no. 28 (August 30, 2011): 5555–63. http://dx.doi.org/10.1002/ejoc.201100940.

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5

Fernando, Roshan, Sandra Pejić, Anna Thomsen, Chunlai Wang, and Geneviève Sauvé. "Azadipyrromethene-based near-IR dyes with styryl substituents at the pyrrolic positions for organic photovoltaic applications." Dyes and Pigments 168 (September 2019): 257–63. http://dx.doi.org/10.1016/j.dyepig.2019.04.067.

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6

Jux, Norbert, Daniel Gryko, Rafał Stężycki, David Reger, and Helen Hoelzel. "Synthesis and Photophysical Properties of Hexaphenylbenzene–Pyrrolo[3,2-b]pyrroles." Synlett 29, no. 19 (September 26, 2018): 2529–34. http://dx.doi.org/10.1055/s-0037-1610286.

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Methods for the synthesis of pyrrolo[3,2-b]pyrroles containing hexaphenylbenzene moieties at the 2- and 5-positions or the 1- and 4-positions have been developed. It was shown that placing a hexaphenylbenzene moiety at the 2- and 5-positions requires a Diels–Alder reaction between an alkyne-substituted pyrrolopyrrole core and a 2,3,4,5-tetraphenylcyclopenta-2,4-dien-1-one. The resulting dyes show a strong blue fluorescence that was hypsochromically shifted by chlorination at the 3- and 6-positions. The overall conjugation between the hexaphenylbenzene moieties and the pyrrolopyrrole core is limited, as evident from their photophysical properties. The hexaphenylbenzene moieties attached to the pyrrolo[3,2-b]pyrrole core could not be transformed into hexa-peri-hexabenzocoronenes through intramolecular oxidative aromatic coupling.

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7

Afsharpour, Maryam, Mehdi Elyasi, and Hamedreza Javadian. "A Novel N-Doped Nanoporous Bio-Graphene Synthesized from Pistacia lentiscus Gum and Its Nanocomposite with WO3 Nanoparticles: Visible-Light-Driven Photocatalytic Activity." Molecules 26, no. 21 (October 29, 2021): 6569. http://dx.doi.org/10.3390/molecules26216569.

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This paper reports the synthesis of a new nitrogen-doped porous bio-graphene (NPBG) with a specific biomorphic structure, using Pistacia lentiscus as a natural carbon source containing nitrogen that also acts as a bio-template. The obtained NPBG demonstrated the unique feature of doped nitrogen with a 3D nanoporous structure. Next, a WO3/N-doped porous bio-graphene nanocomposite (WO3/NPBG-NC) was synthesized, and the products were characterized using XPS, SEM, TEM, FT-IR, EDX, XRD, and Raman analyses. The presence of nitrogen doped in the structure of the bio-graphene (BG) was confirmed to be pyridinic-N and pyrrolic-N with N1 peaks at 398.3 eV and 400.5 eV, respectively. The photocatalytic degradation of the anionic azo dyes and drugs was investigated, and the results indicated that the obtained NPBG with a high surface area (151.98 m2/g), unique electronic properties, and modified surface improved the adsorption and photocatalytic properties in combination with WO3 nanoparticles (WO3-NPs) as an effective visible-light-driven photocatalyst. The synthesized WO3/NPBG-NC with a surface area of 226.92 m2/g displayed lower bandgap and higher electron transfer compared with blank WO3-NPs, leading to an increase in the photocatalytic performance through the enhancement of the separation of charge and a reduction in the recombination rate. At the optimum conditions of 0.015 g of the nanocomposite, a contact time of 15 min, and 100 mg/L of dyes, the removal percentages were 100%, 99.8%, and 98% for methyl red (MR), Congo red (CR), and methyl orange (MO), respectively. In the case of the drugs, 99% and 87% of tetracycline and acetaminophen, respectively, at a concentration of 10 mg/L, were removed after 20 min.

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8

Beverina, Luca, Martin Drees, Antonio Facchetti, Matteo Salamone, Riccardo Ruffo, and Giorgio A. Pagani. "Bulk Heterojunction Solar Cells - Tuning of the HOMO and LUMO Energy Levels of Pyrrolic Squaraine Dyes (Eur. J. Org. Chem. 28/2011)." European Journal of Organic Chemistry 2011, no. 28 (September 21, 2011): n/a. http://dx.doi.org/10.1002/ejoc.201190075.

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9

Xuan, Duc Dau. "Recent Progress in the Synthesis of Pyrroles." Current Organic Chemistry 24, no. 6 (May 25, 2020): 622–57. http://dx.doi.org/10.2174/1385272824666200228121627.

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: Pyrrole derivatives are nitrogen-containing heterocyclic compounds and widely distributed in a large number of natural and non-natural compounds. These compounds possess a broad spectrum of biological activities such as anti-infammatory, antiviral, antitumor, antifungal, and antibacterial activities. Besides their biological activity, pyrrole derivatives have also been applied in various areas such as dyes, conducting polymers, organic semiconductors. : Due to such a wide range of applicability, access to this class of compounds has attracted intensive research interest. Various established synthetic methods such as Paal-Knorr, Huisgen, and Hantzsch have been modified and improved. In addition, numerous novel methods for pyrrole synthesis have been discovered. This review will focus on considerable studies on the synthesis of pyrroles, which date back from 2014.

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10

Fang, Manman, Huiyang Li, Qianqian Li, and Zhen Li. "Co-sensitization of “H”-type dyes with planar squaraine dyes for efficient dye-sensitized solar cells." RSC Advances 6, no. 47 (2016): 40750–59. http://dx.doi.org/10.1039/c6ra03694e.

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The co-sensitized system of “H”-type pyrrole-based dyes and planar squaraine dyes exhibited much improved photovoltaic performance, due to the advantage of the “H” configuration and their complementary spectra.

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11

Gomez, Ana M., and Jose Cristobal Lopez. "Carbohydrates and BODIPYs: access to bioconjugatable and water-soluble BODIPYs." Pure and Applied Chemistry 91, no. 7 (July 26, 2019): 1073–83. http://dx.doi.org/10.1515/pac-2019-0204.

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Abstract Fluorescent difluoroboron dipyrromethenes (BODIPYs), have been accessed in a one-pot synthetic operation from phthalides and pyrroles, a process that involves O-ethylation of phthalides with Meerwein’s reagent (Et3OBF4) and reaction of the ensuing tetrafluoroborate salts with pyrrole, followed by treatment with BF3 · OEt2. These derivatives are endowed with a ortho-hydroxymethyl 8-C-aryl group for further derivatization and/or conjugation to, among others, carbohydrates. The new conjugate derivatives benefit from the optimal characteristics of BODIPYs as fluorescent dyes, including in some instances water-solubility (in the case of conjugation to unprotected carbohydrates). The different kinds of BODIPY-carbohydrate derivatives are compounds of potential interest for biological studies.

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12

Sollert, Carina, Daniel Kocsi, Reuben T. Jane, Andreas Orthaber, and K. Eszter Borbas. "C-glycosylated pyrroles and their application in dipyrromethane and porphyrin synthesis." Journal of Porphyrins and Phthalocyanines 25, no. 07n08 (June 23, 2021): 741–55. http://dx.doi.org/10.1142/s1088424621500723.

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Pyrrole C-glycosylated in either the 2- or the 3-position could be prepared by the acid-catalyzed reaction between trichloroacetimidate glycosyl donors and pyrrole, or [Formula: see text]-phenyl-tri?uoroacetimidate glucosyl donor and [Formula: see text]-TIPS pyrrole, respectively. Pyrroles carrying glucose, mannose, galactose and lactose in the 2-position, and glucose in the 3-position were obtained. The configurations of the products could be assigned using a combination of 1D and 2D NMR spectroscopy. A number of undesired background reactions yielding a variety of stereo- and regioisomers were identified; in several cases these could be eliminated. Glycosylpyrroles could be incorporated into mono- and diglycosylated dipyrromethanes, a diglycosylated BODIPY dye, and a monoglycosylated Zn(II) porphyrin without damaging the sugar unit.

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13

Yen, Yung-Sheng, Ying-Chan Hsu, Jiann T. Lin, Che-Wei Chang, Chao-Ping Hsu, and Da-Jong Yin. "Pyrrole-Based Organic Dyes for Dye-Sensitized Solar Cells." Journal of Physical Chemistry C 112, no. 32 (July 17, 2008): 12557–67. http://dx.doi.org/10.1021/jp801036s.

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14

Xie, Xiao, Michela Zuffo, Marie-Paule Teulade-Fichou, and Anton Granzhan. "Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries." Beilstein Journal of Organic Chemistry 15 (August 6, 2019): 1872–89. http://dx.doi.org/10.3762/bjoc.15.183.

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A library of 52 distyryl and 9 mono-styryl cationic dyes was synthesized and investigated with respect to their optical properties, propensity to aggregation in aqueous medium, and capacity to serve as fluorescence “light-up” probes for G-quadruplex (G4) DNA and RNA structures. Among the 61 compounds, 57 dyes showed preferential enhancement of fluorescence intensity in the presence of one or another G4-DNA or RNA structure, while no dye displayed preferential response to double-stranded DNA or single-stranded RNA analytes employed at equivalent nucleotide concentration. Thus, preferential fluorimetric response towards G4 structures appears to be a common feature of mono- and distyryl dyes, including long-known mono-styryl dyes used as mitochondrial probes or protein stains. However, the magnitude of the G4-induced “light-up” effect varies drastically, as a function of both the molecular structure of the dyes and the nature or topology of G4 analytes. Although our results do not allow to formulate comprehensive structure–properties relationships, we identified several structural motifs, such as indole- or pyrrole-substituted distyryl dyes, as well as simple mono-stryryl dyes such as DASPMI [2-(4-(dimethylamino)styryl)-1-methylpyridinium iodide] or its 4-isomer, as optimal fluorescent light-up probes characterized by high fluorimetric response (I/I 0 of up to 550-fold), excellent selectivity with respect to double-stranded DNA or single-stranded RNA controls, high quantum yield in the presence of G4 analytes (up to 0.32), large Stokes shift (up to 150 nm) and, in certain cases, structural selectivity with respect to one or another G4 folding topology. These dyes can be considered as promising G4-responsive sensors for in vitro or imaging applications. As a possible application, we implemented a simple two-dye fluorimetric assay allowing rapid topological classification of G4-DNA structures.

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15

Portilla Zuniga, Omar Miguel, Angel Gabriel Sathicq, Jose Jobanny Martinez Zambrano, and Gustavo Pablo Romanelli. "Green Synthesis of Pyrrole Derivatives." Current Organic Synthesis 14, no. 6 (September 28, 2017): 865–82. http://dx.doi.org/10.2174/1570179414666161206124318.

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Background: Pyrroles are organic cyclic compounds with an extensive and fascinating chemistry. These compounds have a wide structural variety and they are an important basis in technological development as they can be used as drugs, dyes, catalysts, pesticides, etc. Therefore, the production of these heterocyclic compounds by efficient clean methodologies is a great achievement in contemporary chemistry. In this paper, we show recent green procedures in the synthesis of pyrrole derivatives such as Hantzsch, Knorr and Paal- Knorr syntheses, as well as new eco-friendly synthetic procedures with high efficiency and low environmental impact. Objective: This work focusses on the recent advances in the pyrrole synthesis using clean techniques like ultrasound (US), microwaves (MW), high speed vibration milling (HSVM), catalysts use, solvent replace and other methodologies applied to common reactions to obtain the pyrrole core which follow the green chemistry principles. Conclusion: The main challenge of Green Chemistry is to gradually eliminate the generation of hazardous or harmful materials or replace them with less toxic and safer ones. However, this process must be driven by scientific developments. Its application in the synthesis of heterocyclic compounds such as pyrrole derivatives involves multiple economic and social benefits due to the biological importance of these compounds and their direct impact on the pharmaceutical industry. Although many processes are still under investigation using novel methodologies of green activation such as microwaves, ultrasound and HSVM, as well as synthetic processes in continuous flow and processes at room temperature, promising results such as cost and waste reduction and greater efficiency are achieved.

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16

Lee, Hyun-Young, Jae-Sung Yoo, Hye-Seon Kwon, Jin-Kyu Oh, and Jae-Hong Choi. "Preparation and Characterizations of Solvent Soluble Dyes Based on Dimerized Diketo-pyrrolo-pyrrole Pigment." Molecular Crystals and Liquid Crystals 617, no. 1 (August 13, 2015): 73–81. http://dx.doi.org/10.1080/15421406.2015.1075831.

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17

Poronik, Yevgen M., Leszek M. Mazur, Marek Samoć, Denis Jacquemin, and Daniel T. Gryko. "2,5-Bis(azulenyl)pyrrolo[3,2-b]pyrroles – the key influence of the linkage position on the linear and nonlinear optical properties." Journal of Materials Chemistry C 5, no. 10 (2017): 2620–28. http://dx.doi.org/10.1039/c7tc00276a.

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18

Lee, Hyun-Young, Ji-Hye Kim, Jae-Sung Yoo, Ji-Hye Bae, Chun Yoon, and Jae-Hong Choi. "Synthesis and Thermal Stability of Solvent Soluble Dyes Based on Dimerized Diketo-pyrrolo-pyrrole Pigment." Bulletin of the Korean Chemical Society 35, no. 2 (February 20, 2014): 659–62. http://dx.doi.org/10.5012/bkcs.2014.35.2.659.

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19

Zhao, Jianfeng, Kai Chen, Bing Yang, Yanni Zhang, Caixia Zhu, Yinxiang Li, Qichun Zhang, Linghai Xie, and Wei Huang. "Surficial nanoporous carbon with high pyridinic/pyrrolic N-Doping from sp3/sp2-N-rich azaacene dye for lithium storage." RSC Advances 7, no. 85 (2017): 53770–77. http://dx.doi.org/10.1039/c7ra07850a.

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Dye to carbon: Two rationally designed pyridinic/pyrrolic N-doped porous carbons as anodic materials could be achieved by carbonizing π-conjugated azaacene dye born with high ratio sp³/sp²-N.

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20

Raskolupova, Valeria I., Tatyana V. Popova, Olga D. Zakharova, Anastasia E. Nikotina, Tatyana V. Abramova, and Vladimir N. Silnikov. "Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift." Molecules 26, no. 9 (May 3, 2021): 2679. http://dx.doi.org/10.3390/molecules26092679.

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BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. These are widely used as chemosensors, laser materials, and molecular probes. At the same time, BODIPY dyes have small or moderate Stokes shifts like most other fluorophores. Large Stokes shifts are preferred for fluorophores because of higher sensitivity of such probes and sensors. The new boron containing BODIPY dye was designed and synthesized. We succeeded to perform an annulation of pyrrole ring with coumarin heterocyclic system and achieved a remarkable difference in absorption and emission maximum of obtained fluorophore up to 100 nm. This BODIPY dye was equipped with linker arm and was functionalized with a maleimide residue specifically reactive towards thiol groups of proteins. BODIPY residue equipped with a suitable targeting protein core can be used as a suitable imaging probe and agent for Boron Neutron Capture Therapy (BNCT). As the most abundant protein with a variety of physiological functions, human serum albumin (HSA) has been used extensively for the delivery and improvement of therapeutic molecules. Thiolactone chemistry provides a powerful tool to prepare albumin-based multimodal constructions. The released sulfhydryl groups of the homocysteine functional handle in thiolactone modified HSA were labeled with BODIPY dye to prepare a labeled albumin-BODIPY dye conjugate confirmed by MALDI-TOF-MS, UV-vis, and fluorescent emission spectra. Cytotoxicity of the resulting conjugate was investigated. This study is the basis for a novel BODIPY dye-albumin theranostic for BNCT. The results provide further impetus to develop derivatives of HSA for delivery of boron to cancer cells.

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21

Tasior, Mariusz, Beata Koszarna, David C. Young, Beata Bernard, Denis Jacquemin, Dorota Gryko, and Daniel T. Gryko. "Fe(iii)-Catalyzed synthesis of pyrrolo[3,2-b]pyrroles: formation of new dyes and photophysical studies." Organic Chemistry Frontiers 6, no. 16 (2019): 2939–48. http://dx.doi.org/10.1039/c9qo00675c.

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22

Garcia-Amorós, Jaume, Marta Reig, M. Cidália R. Castro, Alba Cuadrado, M. Manuela M. Raposo, and Dolores Velasco. "Molecular photo-oscillators based on highly accelerated heterocyclic azo dyes in nematic liquid crystals." Chem. Commun. 50, no. 51 (2014): 6704–6. http://dx.doi.org/10.1039/c4cc01450b.

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23

Raskolupova, Valeria I., Tatyana V. Popova, Olga D. Zakharova, Tatyana V. Abramova, and Vladimir N. Silnikov. "New BODIPY Dye with a Large Stokes Shift for Biopolymer Labelling." Chemistry Proceedings 3, no. 1 (November 14, 2020): 72. http://dx.doi.org/10.3390/ecsoc-24-08304.

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As the most abundant protein with a variety of physiological functions, human serum albumin (HSA) has been used extensively for the delivery and improvement of therapeutic molecules. Thiolactone chemistry provides a powerful tool to prepare albumin-based multimodal imaging probes and agents for boron neutron capture therapy (BNCT). For this purpose, boron containing 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dye was designed and synthesized. BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. These are widely used as chemosensors, laser materials and molecular probes. At the same time, BODIPY dyes, like most other fluorophores, have small or moderate Stokes shifts. Large Stokes shifts are preferred for fluorophores because of higher sensitivity of such probes and sensors. We succeeded in performing an annulation of pyrrole ring with coumarin heterocyclic system and achieved a remarkable difference in absorption and emission maximum of obtained fluorophore up to 100 nm. Moreover, this BODIPY dye was equipped with a linker arm and was functionalized with a maleimide residue specifically reactive towards thiol groups of proteins. The released sulfhydryl groups of the homocysteine functional handle in thiolactone modified HSA was labeled with BODIPY dye to prepare a labeled albumin-BODIPY dye conjugate confirmed by MALDI-TOF-MS, UV-vis and fluorescent emission spectra. The cytotoxicity of HSA conjugate was evaluated by MTT assay in cell lines MCF-7 and T98G. This is the basis for a novel BODIPY dye -albumin theranostic for BNCT. These results provide further impetus to develop derivatives of HSA for delivery of boron to cancer cells.

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24

Schutting, Susanne, Sergey M. Borisov, and Ingo Klimant. "Diketo-Pyrrolo-Pyrrole Dyes as New Colorimetric and Fluorescent pH Indicators for Optical Carbon Dioxide Sensors." Analytical Chemistry 85, no. 6 (March 7, 2013): 3271–79. http://dx.doi.org/10.1021/ac303595v.

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25

Choi, Se-Hwa, Ga-Hye Kil, Na-Rim Kim, Chun Yoon, Jae-Pil Kim, and Jae-Hong Choi. "Preparation of Thermally Stable Red Dyes Derived from Diketo-Pyrrolo-Pyrrole Pigment for LCD Color Filter." Molecular Crystals and Liquid Crystals 550, no. 1 (October 18, 2011): 76–82. http://dx.doi.org/10.1080/15421406.2011.600222.

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26

Fernandes, Sara S. M., Maria Cidália R. Castro, Dzmitry Ivanou, Adélio Mendes, and Maria Manuela M. Raposo. "Push-Pull Heterocyclic Dyes Based on Pyrrole and Thiophene: Synthesis and Evaluation of Their Optical, Redox and Photovoltaic Properties." Coatings 12, no. 1 (December 28, 2021): 34. http://dx.doi.org/10.3390/coatings12010034.

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Three heterocyclic dyes were synthesized having in mind the changes in the photovoltaic, optical and redox properties by functionalization of 5-aryl-thieno[3,2-b]thiophene, 5-arylthiophene and bis-methylpyrrolylthiophene π-bridges with different donor, acceptor/anchoring groups. Knoevenagel condensation of the aldehyde precursors with 2-cyanoacetic acid was used to prepare the donor-acceptor functionalized heterocyclic molecules. These organic metal-free dyes are constituted by thieno[3,2-b]thiophene, arylthiophene, bis-methylpyrrolylthiophene, spacers and one or two cyanoacetic acid acceptor groups and different electron donor groups (alkoxyl, and pyrrole electron-rich heterocycle). The evaluation of the redox, optical and photovoltaic properties of these compounds indicate that 5-aryl-thieno[3,2-b]thiophene-based dye functionalized with an ethoxyl electron donor and a cyanoacetic acid electron acceptor group/anchoring moiety displays as sensitizer for DSSCs the best conversion efficiency (2.21%). It is mainly assigned to the higher molar extinction coefficient, long π-conjugation of the heterocyclic system, higher oxidation potential and strong electron donating capacity of the ethoxyl group compared to the pirrolyl moiety.

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27

Wang, Bing, Nannan He, Bo Li, Shuangying Jiang, Yi Qu, Sanyin Qu, and Jianli Hua. "Aggregation-Induced Emission and Large Two-Photon Absorption Cross-Sections of Diketopyrrolopyrrole (DPP) Derivatives." Australian Journal of Chemistry 65, no. 4 (2012): 387. http://dx.doi.org/10.1071/ch11410.

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In this work, a new series of triphenylamine-based diketo-pyrrolo-pyrrole (DPP) compounds (DPP-I, DPP-II, DPP-III) have been designed and synthesized by a concise route. Their one- and two-photon absorption properties have been investigated. It was found that DPP-based compounds are very weakly fluorescent in THF solution, but their intensities are increased by almost 29, 9, and 24 times in water/THF (v/v 90 %) mixtures, respectively, in which they exhibit a strongly enhanced red fluorescence. The result indicates that the intramolecular vibration and rotation of these dyes is considerably restricted in nano-aggregates formed in water/THF mixtures, which leads to significant increases in fluorescence. The two-photon absorption (2PA) cross-sections measured by the open aperture Z-scan technique were determined to be 188, 275 and 447 GM for DPP-I, DPP-II, and DPP-III, respectively; DPP-III with the symmetrical structure shows the highest value of 2PA cross-section. The excellent properties of aggregation-induced emission (AIE) and 2PA provide an attractive alternative for the biophotonic materials.

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28

Choi, Se-Hwa, Oh-Tak Kwon, Na-Rim Kim, Chun Yoon, Jae-Pil Kim, and Jae-Hong Choi. "Preparation of Solvent Soluble Dyes Derived from Diketo-pyrrolo-pyrrole Pigment by Introducing an N-Alkyl group." Bulletin of the Korean Chemical Society 31, no. 4 (April 20, 2010): 1073–76. http://dx.doi.org/10.5012/bkcs.2010.31.04.1073.

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29

Swavey, Shawn, John Quinn, Michael Coladipietro, Kegan G. Cox, and M. Kyle Brennaman. "Tuning the photophysical properties of BODIPY dyes through extended aromatic pyrroles." RSC Advances 7, no. 1 (2017): 173–79. http://dx.doi.org/10.1039/c6ra26331c.

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A series of naphthyl and fluorantho-fused BODIPY dyes have been synthesized by a simple two-step process. These dyes display high molar absorptivities in the far visible region of the spectrum with emission quantum efficiencies at or near unity.

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30

Li, Qianqian, Lanlan Lu, Cheng Zhong, Jing Huang, Qing Huang, Jie Shi, Xianbo Jin, Tianyou Peng, Jingui Qin, and Zhen Li. "New Pyrrole-Based Organic Dyes for Dye-Sensitized Solar Cells: Convenient Syntheses and High Efficiency." Chemistry - A European Journal 15, no. 38 (September 28, 2009): 9664–68. http://dx.doi.org/10.1002/chem.200901150.

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31

Li, Qianqian, Jie Shi, Huiyang Li, Shuang Li, Cheng Zhong, Fulin Guo, Ming Peng, Jianli Hua, Jingui Qin, and Zhen Li. "Novel pyrrole-based dyes for dye-sensitized solar cells: From rod-shape to “H” type." Journal of Materials Chemistry 22, no. 14 (2012): 6689. http://dx.doi.org/10.1039/c2jm30200d.

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32

Choi, Se-Hwa, Ga-Hye Kil, Na-Rim Kim, Chun Yoon, Jae-Pil Kim, and Jae-Hong Choi. "Preparation of Red Dyes Derived from Diketo-pyrrolo-pyrrole Based Pigment and Their Properties for LCD Color Filters." Bulletin of the Korean Chemical Society 31, no. 11 (November 20, 2010): 3427–30. http://dx.doi.org/10.5012/bkcs.2010.31.11.3427.

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33

Briks, Yu L., and N. N. Romanov. "Polymethine dyes based on cyclohepta[c]pyrrole." Chemistry of Heterocyclic Compounds 27, no. 10 (October 1991): 1157–58. http://dx.doi.org/10.1007/bf00486821.

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34

Raposo, M. Manuela M., Ana M. R. C. Sousa, António Maurício C. Fonseca, and Gilbert Kirsch. "Donor-Acceptor Substituted Thienylpyrrole Azo Dyes: Synthesis, Solvatochromic and Electrochemical Properties." Materials Science Forum 514-516 (May 2006): 103–7. http://dx.doi.org/10.4028/www.scientific.net/msf.514-516.103.

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The synthesis of thienyl- substituted pyrrole azo dyes and their UV-visible, solvatochromic and electrochemical properties are described. In agreement with the solvatochromic data and also with the electrochemical study the new donor-acceptor systems synthesized could have applications in NLO.

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35

Younis, Sherif A., Ahmed Abd-Elaziz, and Ahmed I. Hashem. "Utilization of a pyrrole derivative based antimicrobial functionality impregnated onto CaO/g-C3N4 for dyes adsorption." RSC Advances 6, no. 92 (2016): 89367–79. http://dx.doi.org/10.1039/c6ra10143g.

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A novel functionalization of CaO/g-C₃N₄ based nanocomposite using 4,5-diphenyl-2-thioxo-2,5-dihydro-1H-pyrrole-3-cabonitrile (P3C@CaO–HCN) was fabricated for wastewater remediation from organic dyes and microbial pollutants.

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36

Almodôvar, Vitor A. S., and Augusto C. Tomé. "A Convenient Synthesis of Diketopyrrolopyrrole Dyes." Molecules 26, no. 16 (August 6, 2021): 4758. http://dx.doi.org/10.3390/molecules26164758.

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Diketopyrrolo[3,4-c]pyrroles (DPP) are high-performance organic optoelectronic materials. They have applications in solar cells, fluorescent probes, bioimaging, photodynamic/photothermal therapy, and in many other areas. This article reports a convenient two-step synthesis of various DPP dyes from Pigment Red 254, an inexpensive commercial pigment. The synthesis includes a Suzuki–Miyaura cross-coupling reaction of a bis(4-chlorophenyl)DPP derivative with aryl and hetaryl boronic acids under mild reaction conditions. The new dyes show large Stokes shifts and high fluorescence quantum yields, important features for their potential use in technical and biological applications.

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37

Ho, Yuh Wen, and Wei Hua Yao. "Thioxopyrimidine in Heterocyclic Synthesis III: Synthesis and Properties of Some Novel Heterocyclic Chalcone Derivatives Containing a Thieno[2,3-d]pyrimidine-Based Chromophore." Journal of Chemistry 2013 (2013): 1–11. http://dx.doi.org/10.1155/2013/649576.

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Cyclization of 4-methyl-2-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carbonitrile1with chloroacetone in DMF in the presence of excess potassium carbonate anhydrous gave the 1-(5-amino-4-methyl-2-phenylthieno[2,3-d]pyrimidin-6-yl)ethanone3, which can react with 2,5-dimethoxytetrahydrofuran in glacial acetic acid producing the 1-[4-methyl-2-phenyl-5-(1H-pyrrol-1-yl)thieno[2,3-d]pyrimidin-6-yl]ethanone4. On the other hand, a series of novel 3-aryl-1-[4-methyl-2-phenyl-5-(1H-pyrrol-1-yl)-thieno[2,3-d]pyrimidin-6-yl]prop-2-en-1-one chalcone dyes6a—nwere obtained by the condensation reaction of 1-[4-methyl-2-phenyl-5(1H-pyrrol-1-yl)thieno[2,3-d]-pyrimidin-6-yl]ethanone4with appropriate aldehydes. The structures of chalcone dyes were characterized by IR,1H NMR, mass, elemental analysis, and UV-Vis spectroscopy. The dyes were applied to polyester fibers for creating hues ranging from greenish-yellow to orange; their spectral characteristics, substituent effect in DMF solution, fastness properties, and colorimetric assessment are also discussed.

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Tamilavan, Vellaiappillai, Nara Cho, Chulwoo Kim, Jaejung Ko, and Myung Ho Hyun. "Synthesis of triphenylamine-based thiophene-(N-aryl)pyrrole-thiophene dyes for dye-sensitized solar cell applications." Tetrahedron 68, no. 29 (July 2012): 5890–97. http://dx.doi.org/10.1016/j.tet.2012.04.104.

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39

Zhang, Hai, Zafar Iqbal, Zhen-E. Chen, and Yan-Ping Hong. "Effect of structural optimization on the photovoltaic performance of dithieno[3,2-b:2′,3′-d]pyrrole-based dye-sensitized solar cells." RSC Advances 7, no. 57 (2017): 35598–607. http://dx.doi.org/10.1039/c7ra05716d.

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Five novel organic push–pull dyes, DT, CD-T, TD-T, CD-C and TD-P, based on carbazole or triphenylamine as donors, dithieno[3,2-b:2′,3′-d]pyrrole as a π-spacer and cyanoacetic acid as an acceptor were synthesized, and their structures were optimized for DSSCs.

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40

Koçak, Ramazan, and Arif Daştan. "Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles." Beilstein Journal of Organic Chemistry 17 (March 15, 2021): 719–29. http://dx.doi.org/10.3762/bjoc.17.61.

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The synthesis of novel polycyclic π-conjugated dihydropyridazines, pyridazines, and pyrroles was studied. Dihydropyridazine dyes were synthesized by inverse electron-demand Diels–Alder cycloaddition reactions between a dibenzosuberenone and tetrazines that bear various substituents. The pyridazines were synthesized in high yields by oxidation of dihydropyridazine-appended dibenzosuberenones with PIFA or NO. p-Quinone derivatives of pyridazines were also obtained by H-shift isomerization following the inverse electron-demand Diels–Alder reaction of tetrazines with p-quinone dibenzosuberenone. Then these pyridazines were converted to the corresponding pyrroles by reductive treatment with zinc. It was observed that all the dihydropyridazines obtained gave absorbance and emission at long wavelengths.

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41

BRIKS, YU L., and N. N. ROMANOV. "ChemInform Abstract: Polymethine Dyes from Cyclohepta(c)pyrrole." ChemInform 26, no. 10 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199510238.

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42

Choi, Se-Hwa, Ga-hye Kil, Na-rim Kim, Chun Yoon, Jae-Pil Kim, and Jae-Hong Choi. "ChemInform Abstract: Preparation of Red Dyes Derived from Diketo-pyrrolo-pyrrole Based Pigment and Their Properties for LCD Color Filters." ChemInform 42, no. 12 (February 24, 2011): no. http://dx.doi.org/10.1002/chin.201112189.

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43

Li, Feng, Yi-Zhou Zhu, Shao-Chun Zhang, Huan-Huan Gao, Bin Pan, and Jian-Yu Zheng. "Pyrrolo[3,2,1-kl]phenothiazine-based D- π -A type organic dyes for efficient dye-sensitized solar cells." Dyes and Pigments 139 (April 2017): 292–99. http://dx.doi.org/10.1016/j.dyepig.2016.12.025.

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44

Kubota, Yasuhiro, Kenta Koide, Yuka Mizuno, Masato Nakazawa, Toshiyasu Inuzuka, Kazumasa Funabiki, Hiroyasu Sato, and Masaki Matsui. "Synthesis and fluorescence properties of unsymmetrical 1,4-dihydropyrrolo[3,2-b]pyrrole dyes." New Journal of Chemistry 46, no. 4 (2022): 1533–42. http://dx.doi.org/10.1039/d1nj04663b.

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Despite being regioisomers, unsymmetrical 1,4-dihydropyrrolo[3,2-b]pyrroles 5 and 6 showed significantly different absorption and fluorescence properties due to the difference of the resonance structure between 5 and 6.

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45

Kim, Tae-Heon, Byung-Jun Lee, Sung-Ok An, Joo-Hong Lee, and Jae-Hong Choi. "The synthesis of red dyes based on diketo-pyrrolo-pyrrole chromophore to improve heat stability and solubility for colour filter fabrication." Dyes and Pigments 174 (March 2020): 108053. http://dx.doi.org/10.1016/j.dyepig.2019.108053.

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46

Li, Huiyang, Yingqin Hou, Yizhou Yang, Runli Tang, Junnian Chen, Heng Wang, Hongwei Han, Tianyou Peng, Qianqian Li, and Zhen Li. "Attempt to Improve the Performance of Pyrrole-Containing Dyes in Dye Sensitized Solar Cells by Adjusting Isolation Groups." ACS Applied Materials & Interfaces 5, no. 23 (November 21, 2013): 12469–77. http://dx.doi.org/10.1021/am403668d.

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47

Zhang, Chunyao, Shibin Wang, and Yang Li. "Phenothiazine organic dyes containing dithieno[3,2-b:2′,3′-d]pyrrole (DTP) units for dye-sensitized solar cells." Solar Energy 157 (November 2017): 94–102. http://dx.doi.org/10.1016/j.solener.2017.08.012.

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48

Tian, Yi, Xintong Ying, Chunli Zhou, Shupeng Zhang, Siyu Zhao, Ke Li, Mengchen Xu, Hui-Juan Yu, Guang Shao, and Jing-Kun Fang. "Novel organic dyes for dye-sensitized solar cells based on 1-(2-ethylhexyl)pyrrole as a π-bridge." Dyes and Pigments 182 (November 2020): 108655. http://dx.doi.org/10.1016/j.dyepig.2020.108655.

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49

Lempke, Linda, Tobias Fischer, Jérémy Bell, Werner Kraus, Knut Rurack, and Norbert Krause. "Gold-catalyzed allene cycloisomerization for pyrrole synthesis: towards highly fluorinated BODIPY dyes." Organic & Biomolecular Chemistry 13, no. 12 (2015): 3787–91. http://dx.doi.org/10.1039/c4ob02671c.

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50

Meyer, Andreas Uwe, Anna Lucia Berger, and Burkhard König. "Metal-free C–H sulfonamidation of pyrroles by visible light photoredox catalysis." Chemical Communications 52, no. 72 (2016): 10918–21. http://dx.doi.org/10.1039/c6cc06111g.

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