Effect of extended conjugation with a phenylethynyl group on the fluorescence properties of water-soluble arylboronic acids

Abstract

Boronic acids that change fluorescent properties upon sugar binding are very important reporter units for the development of small molecule lectin mimics (boronolectins). Aimed at developing long wavelength fluorescent boronic acid reporter compounds, we have designed and synthesized a series of boronic acid analogs 2a-d with an extended π conjugation. Such designs are based on earlier fluorescent boronic acids that change fluorescent properties upon sugar binding. Compared with the corresponding parent chromophores, these new compounds with extended conjugations show longer excitation and emission wavelengths as designed. The patterns of fluorescent changes for the new compounds are also different from that of the corresponding parent compounds.

A New Class of Fluorescent Boronic Acids That Have Extraordinarily High Affinities for Diols in Aqueous Solution at Physiological pH

“…There have also been quite a few reviews 12,3 and recent research papers 13-14,15-27 on boronic acids that change fluorescent properties upon binding to a nucleophilic/Lewis base analyte.…”

Covalent Interactions in Chemosensor Design

“…Several recent reviews and research papers comprehensively summarize the use of boronic acids in sensor designs for carbohydrates [9,[14][15][16]66], fluoride [47][48][49][50][51], and cyanides [45,46], and have in-depth discussions of factors [15,19,67] that should be considered in designing such sensors. In addition, there have also been quite a few reviews [8,15,66] and research papers [54,[68][69][70][71][72][73][74][75][76][77][78][79][80][81][82][83][84][85] on boronic acids that change their fluorescent properties upon binding to a nucleophilic analyte or pH changes. Obviously, it would not be possible to describe all these findings here; therefore, readers are referred to the above-referenced papers for details.…”

Carbohydrate biomarkers for future disease detection and treatment

“…Several recent reviews and research papers comprehensively summarize the use of boronic acids in sensor designs for carbohydrates [51,54,55,231,239] fluoride [290][291][292][293][294], cyanides [288,289], as well as in-depth discussions of factors [55,263,296] that should be considered along the line of designing such sensors. Besides, there have also been quite a few recent reviews [51,53] and research papers [44,156,[297][298][299][300][301][302][303][304][305][306][307][308][309][310][311][312] on boronic acids that change fluorescent properties upon binding to a nucleophilic analyte or pH changes. Readers are referred to the above-referenced papers for details.…”