NDLI: Effects of cyclodextrins and saccharides on dual fluorescence of N,N-dimethyl-4-aminophenylboronic acid in water

Content Provider	Springer Nature Link
Author	Ozawa, Rimiko Hayashita, Takashi Matsui, Takahiro Nakayama, Chiaki Yamauchi, Akiyo Suzuki, Iwao
Copyright Year	2007
Abstract	N,N-Dimethyl-4-aminophenylboronic acid (DMAPB) showed pH-dependent dual fluorescence at 360 and 462 nm originating from locally excited (LE) and twisted intramolecular charge transfer (TICT) states, respectively, in aqueous solutions. Upon complexation with α-CD, LE fluorescence was markedly increased while TICT fluorescence was decreased. In contrast, both LE and TICT fluorescence were increased when DMAPB was complexed with β-CD. The fluorescence variations enabled us to determine the 1:1 and 1:2 binding constants of the DMAPB/α-CD complex to be 10 and 40 M$^{−1}$, respectively, and the 1:1 binding constant of the DMAPB/β-CD complex to be 635 M$^{−1}$. The dual fluorescence of DMAPB alone was found to be a good indicator of saccharide sensing. Under weakly alkaline conditions, saccharides suppressed TICT fluorescence while increasing LE fluorescence. Among the saccharides investigated, d-fructose induced the largest fluorescence change, followed by d-ribose and d-glucose. This order is consistent with the stability of the boronate esters of DMAPB with saccharides. In the presence of β-CD, saccharide selectivity was unchanged, while fluorescence was amplified. These results demonstrate the superiority of the supramolecular DMAPB/β-CD complex to DMAPB alone as a ratiometric fluorescence sensor for saccharides in water.
Starting Page	253
Ending Page	261
Page Count	9
File Format	PDF
ISSN	09230750
Journal	Journal of Inclusion Phenomena and Macrocyclic Chemistry
Volume Number	60
Issue Number	3-4
e-ISSN	15731111
Language	English
Publisher	Springer Netherlands
Publisher Date	2007-09-15
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Boronic acid Chemical sensor Cyclodextrin Dual fluorescence Saccharide sensing Twisted intramolecular charge transfer Crystallography Food Science Organic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Food Science

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