Regulating the fluorescence intensity of an anthracene boronic acid system: a B–N bond or a hydrolysis mechanism?

Synthesis, Evaluation, and Computational Studies of Naphthalimide‐Based Long‐Wavelength Fluorescent Boronic Acid Reporters

“…[65,66] Other possibilities may also include a change in the specific species formed when going from an aqueous environment to an organic solution. [10,40,41,43,[67][68][69][70] The similar solvent effects on compound 3, which does not have a boronic acid moiety, and boronic acid 1 b indicate that the phenylboronic acid moiety itself does not directly participate in the generation of fluorescence, although the formation of the anionic boronate species (Scheme 3) may influence the fluorescence properties of 1 b (and 1 a, 1 c, and 1 d), which will be discussed in the next section. The similar behaviors among 1 a-d in terms of l max , emission wavelength, pH profiles, and sugar-induced fluorescence changes also suggest that the phenylboronic acid moiety plays only an auxiliary role in fluorescence modulation and is not part of the fluorophore that is responsible for fluorescence generation.…”

“…In this series, an amino group was positioned in a 1,5 relationship to the boronic acid, which helps to modulate its pK a and electronic states. [6,[40][41][42][43] The change in the ionization state of the boron atom upon sugar binding from the neutral sp 2 form to the anionic sp 3 state was thought to be the reason for the observed fluorescence changes. In our previous work, we examined the effect of N substitution on the fluorescence properties of this series of compounds.…”

Supramolekulare Chemie in Wasser

“…[33,34] Die erste Studie zur Saccharidkomplexierung durch Boronsäuren in Wasser erschien schon vor mehr als einem halben Jahrhundert, [35] diese Funktionalität ist aber immer noch aktuell für das Design empfindlicher und selektiver Rezeptoren. [36,37] Der pK S -Wert der Boronsäure, der pH-Wert des wässrigen Mediums und der Einfluss von Substituenten (besonders Aminen, die Komplexe mit Boronsäuren bilden) wurden untersucht, um den Komplexierungsmechanismus zu verstehen und eine mögliche Verwendung in Sensoren abzuwä-gen. [37,38] Etliche Fluoreszenzsensoren für Saccharide enthalten einen Boronsäuresubstituenten. [33] Wegen der hohen Empfindlichkeit der Fluoreszenz können Erkennungs-und Messversuche gewöhnlich bei niedrigen Konzentrationen durchgeführt werden.…”

Effects of Cyclodextrins on Intramolecular Photoinduced Electron Transfer in a Boronic Acid Fluorophore

“…Although chemosensors based on boronic acid are not as selective as enzyme-based sensors, they have attracted much attention because of their greater stabilities. 4,5 Phenylboronic acid can readily form stable cyclic esters with the diol moiety of sugars in water, 6 and various types of boronic acid chemosensors with response mechanisms based on internal charge transfer (ICT), [7][8][9][10] photoinduced electron transfer (PET), [11][12][13] and fluorescent resonance energy transfer (FRET) 14 have been developed. The versatile designs of chemosensors based on supramolecular chemistry are another approach to construct novel sugar sensors.…”