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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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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. |
format | Online Article Text |
id | pubmed-9049792 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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