Click synthesis of a triphenylamine-based fluorescent methanol probe with a unique D-π-A structure

Wu, Zhihua; Fu, Xiangyu; Wang, Yong

doi:10.1016/j.snb.2017.01.164

Cited by 21 publications

(8 citation statements)

References 41 publications

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“…As shown ( Figure 5 a,b), with the concentration increase of 1, the fluorescence intensity of SCAIECD was gradually quenched and the fluorescence was completely diminished when the hydrogenase concentration increased to 0.6 molar equivalent of SCAIECD’s concentration. According to our previous research [ 34 ], when we conducted the titration experiment, a good linear response was found in the low concentration range ( Figure 5 b inset) and the detection limit could be to 3 µM.…”

Section: Resultssupporting

confidence: 55%

Click Access to a Cyclodextrin-Based Spatially Confined AIE Material for Hydrogenase Recognition

Zhao

Wang

et al. 2018

Sensors

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The spatial confinement of conjugated phenyl rotators is a compulsory requirement for the fluorescence enhancement of aggregation induced emission (AIE) molecules. This work reports a novel spatially confined AIE material by restricting several tetraphenylethylene (TPE) molecules around the primary face of β-cyclodextrin (CD) via a Cu(I) catalytic 1,3-dipolar cycloaddition reaction (click chemistry). The spatial confinement effect was found to significantly enhance the fluorescence emission when compared with a single TPE modified CD. In addition, the emission maxima took place with the dimethyl sulfoxide volume ratio of 30% in a water mixture, which is remarkably different from traditional AIE molecules. Benefiting from the CD’s complexation effect, this material exhibits a selective fluorescence quenching property in certain hydrogenases and can be used as a fluorescence probe for hydrogenase sensing. This demonstrates the potential of the spatially confined AIECD for practical applications.

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Section: Resultssupporting

confidence: 55%

Click Access to a Cyclodextrin-Based Spatially Confined AIE Material for Hydrogenase Recognition

Zhao

Wang

et al. 2018

Sensors

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“…In addition, several chemical indicators have been developed in recent years 39 , 40 . However, the number of bona fide colorimetric sensors and reaction-based indicators for methanol that allow its presence to be detected through simple color changes remain limited and selectivity remains an issue 41 – 43 . It is thus possible that the “Twisted–Planar–Twisted” dimer D may have a role to play in addressing this need.…”

Section: Introductionmentioning

confidence: 99%

Twisted-Planar-Twisted expanded porphyrinoid dimer as a rudimentary reaction-based methanol indicator

Baryshnikov

et al. 2020

Nat Commun

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Directly linked porphyrin dimers have attracted considerable attention because of their intriguing electronic features. Most emphasis has been placed on either dimers with large dihedral angles between the constituent planar monomeric subunits or those with overall planarity, referred to as “Planar-Twisted-Planar” and “Planar-Planar-Planar”, respectively. Herein, we report a “Twisted-Planar-Twisted” framework, the hexaphyrin dimer D that exists in a trans configuration. Treatment of D with MeOH affords two isomeric dimers, MD1 and MD2, both of which incorporate a methoxy moiety and exist in cis orientations with respect to the tethering linkage. The methanol-promoted conversion is accompanied by a readily discernible color change from green to brown and is not induced to an appreciable level by other alcohols. Dimer D thus acts as a rudimentary, albeit highly selective, reaction-based methanol indicator. This work provides a promising approach for constructing reaction-based chemosensors using porphyrinoid dimers of nonplanar subunits with biased reactivity.

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“…The group of Wang developed a so-called donor−π-system–acceptor (D−π–A) probe TTO 63 , using click chemistry to form the triazole as a coplanar π–electron bridge between the sensing units . This approach enabled the facile synthesis of several structural analogues.…”

Section: Chromo- and Fluorogenic Probes For Alcoholsmentioning

confidence: 99%

Enlightening the Path to Protein Engineering: Chemoselective Turn-On Probes for High-Throughput Screening of Enzymatic Activity

et al. 2023

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Many successful stories in enzyme engineering are based on the creation of randomized diversity in large mutant libraries, containing millions to billions of enzyme variants. Methods that enabled their evaluation with high throughput are dominated by spectroscopic techniques due to their high speed and sensitivity. A large proportion of studies relies on fluorogenic substrates that mimic the chemical properties of the target or coupled enzymatic assays with an optical read-out that assesses the desired catalytic efficiency indirectly. The most reliable hits, however, are achieved by screening for conversions of the starting material to the desired product. For this purpose, functional group assays offer a general approach to achieve a fast, optical read-out. They use the chemoselectivity, differences in electronic and steric properties of various functional groups, to reduce the number of false-positive results and the analytical noise stemming from enzymatic background activities. This review summarizes the developments and use of functional group probes for chemoselective derivatizations, with a clear focus on screening for enzymatic activity in protein engineering.

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Click synthesis of a triphenylamine-based fluorescent methanol probe with a unique D-π-A structure

Cited by 21 publications

References 41 publications

Click Access to a Cyclodextrin-Based Spatially Confined AIE Material for Hydrogenase Recognition

Click Access to a Cyclodextrin-Based Spatially Confined AIE Material for Hydrogenase Recognition

Twisted-Planar-Twisted expanded porphyrinoid dimer as a rudimentary reaction-based methanol indicator

Enlightening the Path to Protein Engineering: Chemoselective Turn-On Probes for High-Throughput Screening of Enzymatic Activity

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