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

Gi Hun Bae; Suzi Kim; Na Keum Lee; Anuradha Dagar; Jeong Hwa Lee; Jeeyeon Lee; Ikyon Kim

doi:10.1039/d0ra01140a

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

Gi Hun Bae, Suzi Kim, Na Keum Lee, Anuradha Dagar, Jeong Hwa Lee, Jeeyeon Lee, Ikyon Kim

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	7265-7288
Number of pages	24
Journal	RSC Advances
Volume	10
Issue number	12
DOIs	https://doi.org/10.1039/d0ra01140a
Publication status	Published - 2020 Feb

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (NRF-2017R1A2A2A05069364 and NRF-2018R1A6A1A03023718) to I. K. and the National Research Foundation of Korea (NRF) grants funded by the Korean government (MSIP) (NRF-2018R1A2B2005535 and 2018R1A4A1021703) to J. L. We acknowledge Ounyoung Lim for contribution in Operetta High-Content imaging data.

Publisher Copyright:
© 2020 The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

Chemistry(all)
Chemical Engineering(all)

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10.1039/d0ra01140a

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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",

abstract = "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.",

author = "Bae, {Gi Hun} and Suzi Kim and Lee, {Na Keum} and Anuradha Dagar and Lee, {Jeong Hwa} and Jeeyeon Lee and Ikyon Kim",

note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (NRF-2017R1A2A2A05069364 and NRF-2018R1A6A1A03023718) to I. K. and the National Research Foundation of Korea (NRF) grants funded by the Korean government (MSIP) (NRF-2018R1A2B2005535 and 2018R1A4A1021703) to J. L. We acknowledge Ounyoung Lim for contribution in Operetta High-Content imaging data. Publisher Copyright: {\textcopyright} 2020 The Royal Society of Chemistry.",

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AU - Kim, Suzi

AU - Lee, Na Keum

AU - Dagar, Anuradha

AU - Lee, Jeong Hwa

AU - Lee, Jeeyeon

AU - Kim, Ikyon

N1 - Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (NRF-2017R1A2A2A05069364 and NRF-2018R1A6A1A03023718) to I. K. and the National Research Foundation of Korea (NRF) grants funded by the Korean government (MSIP) (NRF-2018R1A2B2005535 and 2018R1A4A1021703) to J. L. We acknowledge Ounyoung Lim for contribution in Operetta High-Content imaging data. Publisher Copyright: © 2020 The Royal Society of Chemistry.

PY - 2020/2

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N2 - 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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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

Abstract

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