Development of a novel chromophore reaction-based fluorescent probe for biogenic amines detection

Abstract

Biogenic amines (BAs) are important biomarkers to monitor meat spoilage. However, design of efficient BAs fluorescent probes with distinct colorimetric and ratiometric fluorescent dual-channels is still a critical challenge because...

A novel windmill-shaped AIE-active pyrrolopyrrole cyanine: design, synthesis and efficient hydrazine detection

“…Moreover, extended absorption and emission maxima at 751 and 825 nm were obtained due to the π-conjugation between the PPCy core and triphenylethylene wing. Compared to our previously reported alkoxyphenyl-modified PPCy ( PPCy-1 , Scheme 1), 14 PPCy-TBE showed a 56 and 100 nm redshift in the absorption and emission maxima, respectively. Meanwhile, PPCy-TBE exhibited an increased Stokes shift compared to PPCy-1 (24–31 nm).…”

“…To reveal the role of the AIE rotor in PPCy, PPCy-1 containing two alkoxyphenyl wings at the perimeter of the PPCy core as a control compound was also synthesized according to our previous method. 14 In CH 2 Cl 2 , PPCy-TBE exhibited an intense absorption band at 742 nm and three moderate absorption bands at 674, 609 and 318 nm (Fig. 1(a)).…”

“…Compounds 4 and PPCy-1 were prepared according to our previous method, 14 as shown in Scheme S1 (ESI †).…”

“…As a new class of NIR dyes and fluorophores, pyrrolopyrrole cyanines (PPCys) exhibit narrow band absorption between 650 and 900 nm and NIR fluorescence emission with high quantum yields. [1][2][3][4][5] By virtue of their high photostability and specific spectral properties (such as negligible absorption in the visible spectral region, high extinction coefficients, and high fluorescence quantum yields), their potential applications including fluorescence bioimaging, [6][7][8][9][10][11][12][13] amine detection, 14 pH indicators, 15,16 organic light-emitting diodes (OLEDs) 17,18 and others 20 have been widely investigated. However, they suffer from a strong aggregation caused quenching (ACQ) effect in aggregate and film states because planar PPCy dyes easily form intermolecular p-p stacking.…”

Recent Advances in Fluorescent Methods for Polyamine Detection and the Polyamine Suppressing Strategy in Tumor Treatment

“…The aza -Michael addition reaction between α,β-unsaturated nitrile and primary amines can proceed smoothly under mild conditions. The pyrrolopyrrole cyanine dye ( 8 ) contained α,β-unsaturated nitrile as Michael acceptors, which was further appended with a withdrawing boron atom to enhance the aza -Michael addition reactivity [ 64 ]. Through this strategy, a highly efficient fluorescent polyamine probe was developed.…”