NDLI: Synthesis of yellow and red fluorescent 1,3a,6a-triazapentalenes and the theoretical investigation of their optical properties

Content Provider	Royal Society of Chemistry (RSC)
Author	Mera, Akane Namba, Kosuke Osawa, Ayumi Taketsugu, Tetsuya Tano, Fumi Chuman, Yoshiro Tanino, Keiji Nakayama, Akira Sakuda, Eri Sakaguchi, Kazuyasu Kitamura, Noboru
Copyright Year	2015
Abstract	To expand the originally developed fluorescent 1,3a,6a-triazapentalenes as fluorescent labelling reagents, the fluorescence wavelength of the 1,3a,6a-triazapentalenes was extended to the red color region. Based on the noteworthy correlation of the fluorescence wavelength with the inductive effect of the 2-substituent, electron-deficient 2-(2-cyano-4-methoxycarbonylphenyl)-1,3a,6a-triazapentalene and 2-(2,6-dicyano-4-methoxycarbonylphenyl)-1,3a,6a-triazapentalene were synthesized. The former exhibited yellow fluorescence and the latter exhibited red fluorescence, and both compounds exhibited large Stokes shifts, and the 1,3a,6a-triazapentalene system enabled the same fluorescent chromophore to cover the entire region of visible wavelengths. The potential applications of the 1,3a,6a-triazapentalenes as fluorescent probes in the fields of the life sciences were investigated, and the 1,3a,6a-triazapentalene system was clearly proven to be useful as a fluorescent reagent for live cell imaging. Quantum chemical calculations were performed to investigate the optical properties of the 1,3a,6a-triazapentalenes. These calculations revealed that the excitation involves a significant charge-transfer from the 1,3a,6a-triazapentalene skeleton to the 2-substituent. The calculated absorption and fluorescence wavelengths showed a good correlation with the experimental ones, and thus the system could enable the theoretical design of substituents with the desired optical properties.
Starting Page	1083
Ending Page	1093
Page Count	11
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	6
Issue Number	2
Journal	Chemical Science
DOI	10.1039/c4sc02780a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Computational chemistry Stokes Red Color List of life sciences Fluorescence Substituent Reagent Wavelength Chromophore
Content Type	Text
Resource Type	Article
Subject	Chemistry

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