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Different mechanisms for the emission turn-on of ortho-aminomethylphenylboronic acids with appended fluorophores in response to saccharide binding in aqueous media have been postulated, such as photoinduced electron transfer (PET), "pK a switch", and disaggregation. However, none of the hypotheses is consistent with all the data for boronic acid-based sensors. To create a unifying theory that can explain the data, we performed a series of experiments to explore the origin of the emission turn-on with several boronic-acid based sensors upon binding fructose. First, we showed that the receptors and their complexes with fructose are solvent-inserted, with no B-N interactions. Second, we verified that the sensors are not aggregated. Third, in pure methanol, that exchanges -B(OH) 2 to -B(OMe) 2 groups, we found no fluorescence response upon binding fructose. We propose this occurs via lessening of internal conversion mechanisms. To investigate this proposal further, we performed a solvent isotope effect study. The fluorescence of the probes in D 2 O (-B(OH) 2 → -B(OD) 2 ) does not change upon fructose binding. It is well accepted that -OD oscillators are less efficient energy acceptors due to their lower frequency vibrational modes. Thus, our studies reveal that modulating the -B(OH) 2 -induced internal conversion (an example of a "loose bolt effect") explains how potentially all ortho-aminomethylphenylboronic acid-based fluorescence sensors signal the presence of sugars.

journal of the american chemical society

Arresting “Loose Bolt” Internal Conversion from −B(OH)<sub>2</sub> Groups is the Mechanism for Emission Turn-On in <i>ortho</i>-Aminomethylphenylboronic Acid-Based Saccharide Sensors

Arresting “Loose Bolt” Internal Conversion from −B(OH)2 Groups is the Mechanism for Emission Turn-On in ortho-Aminomethylphenylboronic Acid-Based Saccharide Sensors

Arresting “Loose Bolt” Internal Conversion from −B(OH)₂ Groups is the Mechanism for Emission Turn-On in ortho-Aminomethylphenylboronic Acid-Based Saccharide Sensors