Switch‐ON Near IR Fluorescent Dye Upon Protonation: Helically Twisted Bis(Boron Difluoride) Complex of π‐Extended Corrorin
| Autor: | Dongho Kim, Shigeki Mori, Hiroyuki Furuta, Masatoshi Ishida, Keiichi Nishimura, Yutaka Hisamune, Taeyeon Kim, Motoki Toganoh |
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| Rok vydání: | 2018 |
| Předmět: |
Circular dichroism
010405 organic chemistry Chemistry Organic Chemistry chemistry.chemical_element Protonation General Chemistry 010402 general chemistry 01 natural sciences Fluorescence Catalysis 0104 chemical sciences Crystallography chemistry.chemical_compound Excited state Ultrafast laser spectroscopy BODIPY Spectroscopy Boron |
| Zdroj: | Chemistry – A European Journal. 24:4628-4634 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.201705516 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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