1394394-98-9

Upstream product

• 40231-03-6 2-(trimethylsilylethynyl)thiophene 
• 436-59-9 dimesitylfluoroborane 
• 1394394-96-7 2-(dimesitylboryl)-5-(trimethylsilylethynyl)thiophene 
• 383913-07-3 2-bromo-1,3-diethyl-2,3-dihydro-1H-1,3,2-benzodiazoborole 
• 1394394-97-8 2-(dimesitylboryl)-5-(ethynyl)thiophene 

Downstream Products

• 1394394-95-6 C₃₄H₃₈B₂FN₂S^(1-)*C₁₆H₃₆N⁽¹⁺⁾ 

Relevant academic research and scientific papers

Diazaborolyl-boryl push-pull systems with ethynylene-arylene bridges as 'turn-on' fluoride sensors

Two linear π-conjugated systems with 1,3-diethyl-1,3,2-benzodiazaborolyl [C6H4(NEt)2B-] as a donor group and dimesitylboryl (-BMes2) as acceptor were synthesised with -ethynylene-phenylene- (-CC-1,4-C6H4-, 3) and -ethynylene-thiophene- (-CC-2,5-C4H2S- 12) bridges between the boron atoms. An assembly (20) consisting of two diazaborolyl-ethynylene- phenylene-boryl units, [C6H4(NCy)(N′)B-CC-1,4-C 6H4-BMes2] joined via a 1,4-phenylene unit at the nitrogen atoms (N′) of the diazaborolyl units was also synthesised. The three push-pull systems, 3, 12 and 20, form salts on fluoride addition with the BMes2 groups converted into (BMes2F)- anions. The molecular structures of 3, 12 and (NBu4)(12·F) were elucidated by X-ray diffraction analyses. The borylated systems 3, 12 and 20 show intense blue luminescence in cyclohexane with quantum yields (Φfl) of 0.99, 0.44 and 0.94, respectively, but weak blue-green luminescence in tetrahydrofuran (Φfl = 0.02-0.05). The charge transfer nature of these transitions is supported by TD-DFT computations with the CAM-B3LYP functional. Addition of tetrabutylammonium fluoride to tetrahydrofuran solutions of 3 and 20 resulted in strong violet-blue luminescence with emission intensities up to 46 times more than the emission intensities observed prior to fluoride addition. Compounds 3 and 20 are demonstrated here as remarkable 'turn-on' fluoride sensors in tetrahydrofuran solutions.