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Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission

A modular approach to polycyclic N-fused heteroaromatics is described. Acid-catalyzed reactions of various 1-(2-oxo-2-arylethyl)-1H-pyrrole-2-carbaldehydes with several o-phenylenediamines provided facile access to a number of new benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through do...

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Autores principales: Bae, Gi Hun, Kim, Suzi, Lee, Na Keum, Dagar, Anuradha, Lee, Jeong Hwa, Lee, Jeeyeon, Kim, Ikyon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9049792/
https://www.ncbi.nlm.nih.gov/pubmed/35493917
http://dx.doi.org/10.1039/d0ra01140a
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author Bae, Gi Hun
Kim, Suzi
Lee, Na Keum
Dagar, Anuradha
Lee, Jeong Hwa
Lee, Jeeyeon
Kim, Ikyon
author_facet Bae, Gi Hun
Kim, Suzi
Lee, Na Keum
Dagar, Anuradha
Lee, Jeong Hwa
Lee, Jeeyeon
Kim, Ikyon
author_sort Bae, Gi Hun
collection PubMed
description A modular approach to polycyclic N-fused heteroaromatics is described. Acid-catalyzed reactions of various 1-(2-oxo-2-arylethyl)-1H-pyrrole-2-carbaldehydes with several o-phenylenediamines provided facile access to a number of new benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization. Optical characterization of the synthesized compounds revealed unique emission properties, with deep blue emission in the aggregated and solid states, and a dramatic substituent effect was observed. Fusion of an additional benzene ring into the benzo[4,5]imidazo[1,2-a]pyrrolo[2,1-c]pyrazine scaffold resulted in a remarkable increase in the intensity of blue fluorescence from the solution along with good cell permeability and negligible phototoxicity, indicating the potential for bioimaging applications.
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spelling pubmed-90497922022-04-29 Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission Bae, Gi Hun Kim, Suzi Lee, Na Keum Dagar, Anuradha Lee, Jeong Hwa Lee, Jeeyeon Kim, Ikyon RSC Adv Chemistry A modular approach to polycyclic N-fused heteroaromatics is described. Acid-catalyzed reactions of various 1-(2-oxo-2-arylethyl)-1H-pyrrole-2-carbaldehydes with several o-phenylenediamines provided facile access to a number of new benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization. Optical characterization of the synthesized compounds revealed unique emission properties, with deep blue emission in the aggregated and solid states, and a dramatic substituent effect was observed. Fusion of an additional benzene ring into the benzo[4,5]imidazo[1,2-a]pyrrolo[2,1-c]pyrazine scaffold resulted in a remarkable increase in the intensity of blue fluorescence from the solution along with good cell permeability and negligible phototoxicity, indicating the potential for bioimaging applications. The Royal Society of Chemistry 2020-02-18 /pmc/articles/PMC9049792/ /pubmed/35493917 http://dx.doi.org/10.1039/d0ra01140a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Bae, Gi Hun
Kim, Suzi
Lee, Na Keum
Dagar, Anuradha
Lee, Jeong Hwa
Lee, Jeeyeon
Kim, Ikyon
Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission
title Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission
title_full Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission
title_fullStr Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission
title_full_unstemmed Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission
title_short Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission
title_sort facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9049792/
https://www.ncbi.nlm.nih.gov/pubmed/35493917
http://dx.doi.org/10.1039/d0ra01140a
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