Synthesis and Spectroscopic Properties of 1,2,3-Triazole BOPAHY Dyes and Their Water-Soluble Triazolium Salts

Abstract

Water-soluble BOPAHY fluorophores have not yet been reported. The potential of 1,2,3-triazolium salts for the formation of water-soluble chromophores is explored. 1,2,3-Triazole-substituted pyrroles were synthesized in a metal-free pathway and alkylated to obtain water-soluble 1,2,3-triazolium BOPAHY dyes. High fluorescence quantum yields were observed for triazole-bridged BOPAHY dyes in DCM and moderate fluorescence quantum yields for 1,2,3-triazolium-bridged BOPAHY chromophores in DCM and water. The fluorescence of the freely rotatable 1,2,3-triazolium-linked BOPAHYs is partially quenched in water.

New Thienobenzo/Naphtho-Triazoles as Butyrylcholinesterase Inhibitors: Design, Synthesis and Computational Study

“…Hence, developing a different synthetic route is very profitable in the long run. According to the literature [ 25 , 26 , 27 ], in the first step, a solution of tetrahydrothianaphthene in toluene, with 1-azido-4-nitro-benzene, the corresponding amine, acetic acid, and 4 Å molecular sieves as a reaction mixture was stirred at 100 °C overnight, then worked up and purified to obtain final products, non-aromatized dihydro-thienobenzo-triazoles 13 – 19 ( Scheme 2 , 27–57%). In the second step, the dihydro derivatives 13 – 19 were aromatized using DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) in dioxane by stirring the reaction mixture at 70 °C overnight, then working it up and purifying it to obtain the final product, aromatized thienobenzo-triazoles 4 , 7 – 12 ( Scheme 2 , see also Section 3 ).…”

Synthesis and photophysical properties of (post-)functionalized BOAHY dyes with strong aggregation-induced emission

“…Notably, post-functionalized BOAHYs 2f and 2g (as shown in Scheme 2) were efficiently derived from 2d and 2e, which possess a bromide functional group. The structures of all compounds 2a-2g were confirmed through high-resolution mass spectrometry and various NMR spectroscopic techniques including 1 H, 11 B, 13 C, and 19 F NMR spectroscopy, most of them were further confirmed by single X-ray crystallography (see ESI †).…”

“…3,4 Furthermore, owing to its strong electron-withdrawing effect, the difluoroboron group can facilitate intramolecular charge transfer (ICT), leading to small bandgaps and long absorption and emission wavelengths. [4][5][6][7][8] The benefits of incorporating this difluoroboron moiety have fueled the development of a multitude of organoboron compounds, including BODIPY, 2,9,10 BOPAHY, [11][12][13] BOPHY 14,15 and BOPPY 16 derivatives (Fig. 1).…”

“…As such, these compounds are the monochelated form of the BOPAHY dyes, which coordinate two difluoroboron groups through an unsymmetrical combination of N-B-N and N-B-O bridges and which were investigated earlier by both our group as well as Jiao's. [11][12][13]44 In this context, a series of new BOAHY derivates are presented here. Almost nonfluorescent in solution, these dyes show considerable fluorescence in the solid state, with fluorescence quantum yields up to 33%.…”

Recent advances in the synthesis of luminescent tetra-coordinated boron compounds

“…232 Indole-pyridine, hydrazine, pyrrolyl-acylhydrazone, bipyridyl, pyridyl pyrrolide and semihemiporphyrazine based boron compounds were also studied for their tuneable photophysical properties. [237][238][239][240][241][242][243][244][245][246]…”