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

Research output: Contribution to journalArticlepeer-review

7 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 languageEnglish
Pages (from-to)7265-7288
Number of pages24
JournalRSC Advances
Volume10
Issue number12
DOIs
Publication statusPublished - 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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