Switch-ON Near IR Fluorescent Dye Upon Protonation: Helically Twisted Bis(Boron Difluoride) Complex of π-Extended Corrorin

Yutaka Hisamune, Taeyeon Kim, Keiichi Nishimura, Masatoshi Ishida, Motoki Toganoh, Shigeki Mori, Dongho Kim, Hiroyuki Furuta

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

A novel helically twisted π-extended corrorin derivative having two boron dipyrrin (BODIPY) moieties at the periphery, a BODIPY DYEmer (6-BF2) cross-bridged with π-conjugated dipyrrinylidene unit, was synthesized and characterized. The neutral 6-BF2 is nonfluorescent due to the internal photoinduced charge transfer (CT) character in the excited state as inferred from the femtosecond transient absorption spectroscopy. However, upon protonation, the CT process is suppressed and the species H6-BF2 + becomes near infrared (IR) emissive. With the aid of rigid helical conformations in 6-BF2, the helical isomers (P- and M-forms) were resolved and their chiroptical property was investigated. The distinct circular dichroism (CD) spectral changes of the enantiomers were observed in the presence of acids, which demonstrates that 6-BF2 can be utilized for potential acid-responsive chiroptical materials.

Original languageEnglish
Pages (from-to)4628-4634
Number of pages7
JournalChemistry - A European Journal
Volume24
Issue number18
DOIs
Publication statusPublished - 2018 Mar 26

Bibliographical note

Funding Information:
The present work in Japan was supported by JSPS KAKENHI Grant Numbers JP15K13646 (HF), JP16K05700 (MI), JP17H05377 (MI). YH thanks to the JSPS Fellowship for Young Scientists. The financial support from a bilateral program between JSPS and the National Research Foundation (NRF) of South Africa is also acknowledged. The work in Korea was supported by Global Research Laboratory (2013K1A1A2A02050183) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT (Information and Communication Technologies) and Future Planning.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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