NDLI: 5-[4-(Dimethylamino)phenyl]-2-benzamidopyrazines: fluorescent dyes based on Cypridina oxyluciferin

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5-[4-(Dimethylamino)phenyl]-2-benzamidopyrazines: fluorescent dyes based on Cypridina oxyluciferin

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5-[4-(Dimethylamino)phenyl]-2-benzamidopyrazines: fluorescent dyes based on Cypridina oxyluciferin

Content Provider	Springer Nature Link
Author	Hira, Takashi Nakagawa, Tatsuki Kodaka, Ai Maki, Shojiro Niwa, Haruki Yamaji, Miru
Copyright Year	2012
Abstract	To clarify the acyl substitution effect on the fluorescent property of Cypridina oxyluciferin analogs, which have the 4-(dimethylamino)phenyl group at C5, we compared the spectroscopic properties of benzamide 1b and its 2,6-dimethylphenyl derivative 1c in various solvents with those of acetamide 1a. Similarity of the fluorescence wavelengths of 1a–c indicates that the π-electronic conjugation in the excited singlet (S$_{1}$) state is terminated at the acyl group and that the benzamide moiety in 1b has little effect on modulating the florescence color. The similar fluorescence solvatochromism of 1a–c reveals that their S$_{1}$ states have a similar intramolecular charge transfer character. The fact that 1a–c have various fluorescence quantum yields and lifetimes depending on solvent polarity and hydrogen bonding interactions in solutions provides information about the decay processes competing with the fluorescence process in the S$_{1}$ states. Among 1a–c, benzamide 1b exhibits the most sensitive variation of the fluorescence intensity depending on the solvent used. Similarity of the fluorescence spectra of 1a–c adsorbed in NaY zeolites was also observed, which indicates that the S$_{1}$ states of 1a–c give mobile conformers in the NaY supercages. The relationship between the molecular structures of 1a–c and their spectroscopic properties will provide a guide for designing a new fluorophore based on Cypridina oxyluciferin.
Starting Page	233
Ending Page	245
Page Count	13
File Format	PDF
ISSN	09226168
Journal	Research on Chemical Intermediates
Volume Number	39
Issue Number	1
e-ISSN	15685675
Language	English
Publisher	Springer Netherlands
Publisher Date	2012-06-14
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Cypridina bioluminescence Oxyluciferin Fluorescence Solvatochromism Intramolecular charge transfer Zeolite Catalysis Physical Chemistry Inorganic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry

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