Boronic acid based photoinduced electron transfer (PET) fluorescence sensors for saccharides

Fluorescence sensor for water based on PET (photo-induced electron transfer): Anthracene-bis(aminomethyl)phenylboronic acid ester

“…The anthracene-bis(aminomethyl)phenylboronic acid ester OA-1 and OA-2 were prepared by the reaction of 9,10-bis(methylaminomethyl)anthracene [37] with 2-bromomethylphenylboronic acid pinacol ester 1 and 2-bromomethyl-4-cyanophenylboronic acid pinacol ester 2 [23] , respectively (Scheme 2). Table 1).…”

“…A solution of 9,10-bis(methylaminomethyl)anthracene (0.3 g, 1.1 mmol) [37] , 1 (1.0 g, 3.4 mmol), Na 2 CO 3 (0.48 g, 4.5 mmol) and DMF (40 ml) was stirred for 2 days at 80 ºC under an …”

“…When the nitrogen atom of amino moiety is protonated or strongly interacts with a cation, a drastic enhancement of fluorescence is observed because of the inhibition of PET. On the basis of PET concept, an anthracene-phenylboronic acid system has been developed by Shinkai group [34][35][36][37] and Wang group [38][39][40] as the fluorescence PET sensor for saccharides. On the other hand, their anthracene-phenylboronic acid system inspired us to conceive an anthracenephenylboronic acid ester OM-1 and OF-2 as a new fluorescence PET sensor for water (Scheme 1).…”

An extended-gate type organic field effect transistor functionalised by phenylboronic acid for saccharide detection in water

“…3 shows the transfer characteristics of the OFET upon titration with phosphate buffer solutions 19 of saccharides. James et al reported a similar selectivity of saccharides using diboronic acid fluorescent photo-induced electron transfer sensors, 3 implying that the SAM formed from PBAs on the extended-gate might bind to glucose with the bis(boronate) complex. 3 exhibits no significant changes in the gate-source current (I GS -V GS ), indicating that electrochemical reactions did not occur at the gate.…”

“…1 For example, glucose is the primary source of metabolic energy in cells. 3 Therefore, a significant amount of attention is being devoted to the development of saccharide sensors for use in healthcare applications. 2 For example, diabetes mellitus has now spread globally and causes complications such as blindness, heart disease, apoplectic stroke and kidney failure.…”