Highly sensitive and selective fluorometric off–on K+ probe constructed via host–guest molecular recognition and aggregation-induced emission

Abstract

In this work, we integrated the concept of aggregation-induced emission (AIE) with the specific supramolecular recognition between K + ions and crown ether moieties to develop more effective fluorometric K + probes. We synthesized a novel crown ether-functionalized tetraphenylethene (TPE) derivative, TPE-(B15C5) 4 , via the thiol-ene click reaction of thiol-derivatized TPE, TPE-(SH) 4 , with maleimide-functionalized benzo-15-crown-5 (B15C5). In TPE-(B15C5) 4 , the TPE core and four outer B15C5 moieties serve as the AIE-active motif and supramolecular K + -recognizing functionalities, respectively. TPE-(B15C5) 4 molecularly dissolves in THF with negligible fluorescence emission. As we have envisaged, upon K + addition, TPE-(B15C5) 4 can be effectively induced to aggregate due to K + -mediated cross-linking via the formation of K + /B15C5 (1/2 molar ratio) molecular recognition complex in a sandwiched manner. This process is concomitantly accompanied with the turn-on of fluorescence emission via the AIE mechanism. Thus, TPE-(B15C5) 4 can serve as highly sensitive and selective fluorometric off-on K + probes.

Design of turn-on fluorescent probe for effective detection of Hg2+ by combination of AIEE-active fluorophore and binding site

“…A c c e p t e d M a n u s c r i p t 6 predicting an absorption wavelength of 458 nm, which is reasonably close to the experimentally obtained absorption peak at 465 nm in tetrahydrofuran solution. The electron cloud density of highest occupied and lowest unoccupied orbital (HOMO and LUMO) were obtained based on the results of TD-DFT using the optimized structure of 1 in the S 0 state.…”

“…Fluorescence chemosensor is regarded as the desirable method due to its advantages of high sensitivity and selectivity, low price, and simple preparation procedures of sample [4][5][6][7]. However, the luminophor molecules, usually tend to aggregate in aqueous solution or bonding with heavy metal ions, leading to the notorious aggregation-caused quenching (ACQ) [8,9].…”

A new approach to developing diagnostics and therapeutics: Aggregation‐induced emission‐based fluorescence turn‐on

“…AIEgens are promising and a variety of AIEgens have been applied to various fields because of advantages such as high brightness, excellent photostability, and large Stokes shift. For example, they can be used to develop high‐performance organic light‐emitting diodes and chemical sensors . Additionally, the most appealing applications of AIEgens are in the field of biological science.…”

“…For example, they can be used to develop high-performance organic light-emitting diodes 158 and chemical sensors. [159][160][161] Additionally, the most appealing applications of AIEgens are in the field of biological science. For pathologists, they can apply AIE probes for discrimination of lesions from normal tissues.…”

A new pyrene-based aggregation induced ratiometric emission probe for selective detections of trivalent metal ions and its living cell application

“…Tang et al have extensively studied the AIE phenomena over the last decade and reported the first AIE-based sensors, in which tetraphenylethene moiety is the most frequently used example of AIE [2,[17][18][19][20][21][22][23][24][25][26][27][28][29]. Some moieties with AIE appearances in stimuli-responsive nano-materials and active layers of efficient organic light emitting diodes have also been found to serve as sensors [30,31].…”