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

Weber L, Eickhoff D, Kahlert J, Böhling L, Brockhinke A, Stammler H-G, Neumann B, Fox MA (2012)
Journal of the Chemical Society. Dalton Transactions 41(34): 10328-10346.

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Abstract
Two linear pi-conjugated systems with 1,3-diethyl-1,3,2-benzodiazaborolyl [C6H4(NEt)(2)B-] as a donor group and dimesitylboryl (-BMes(2)) as acceptor were synthesised with -ethynylene-phenylene-(-C C-1,4-C6H4-, 3) and -ethynylene-thiophene-(-C C-2,5-C4H2S-12) bridges between the boron atoms. An assembly (20) consisting of two diazaborolyl-ethynylene-phenylene-boryl units, [C6H4(NCy)-(N')B-C C-1,4-C6H4-BMes(2)] 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 BMes(2) groups converted into (BMes(2)F)(-) anions. The molecular structures of 3, 12 and (NBu4)(12 center dot F) were elucidated by X-ray diffraction analyses. The borylated systems 3, 12 and 20 show intense blue luminescence in cyclohexane with quantum yields (Phi(fl)) of 0.99, 0.44 and 0.94, respectively, but weak blue-green luminescence in tetrahydrofuran (Phi(fl) = 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.
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Weber L, Eickhoff D, Kahlert J, et al. Diazaborolyl-boryl push-pull systems with ethynylene-arylene bridges as 'turn-on' fluoride sensors. Journal of the Chemical Society. Dalton Transactions. 2012;41(34):10328-10346.
Weber, L., Eickhoff, D., Kahlert, J., Böhling, L., Brockhinke, A., Stammler, H. - G., Neumann, B., et al. (2012). Diazaborolyl-boryl push-pull systems with ethynylene-arylene bridges as 'turn-on' fluoride sensors. Journal of the Chemical Society. Dalton Transactions, 41(34), 10328-10346.
Weber, L., Eickhoff, D., Kahlert, J., Böhling, L., Brockhinke, A., Stammler, H. - G., Neumann, B., and Fox, M. A. (2012). Diazaborolyl-boryl push-pull systems with ethynylene-arylene bridges as 'turn-on' fluoride sensors. Journal of the Chemical Society. Dalton Transactions 41, 10328-10346.
Weber, L., et al., 2012. Diazaborolyl-boryl push-pull systems with ethynylene-arylene bridges as 'turn-on' fluoride sensors. Journal of the Chemical Society. Dalton Transactions, 41(34), p 10328-10346.
L. Weber, et al., “Diazaborolyl-boryl push-pull systems with ethynylene-arylene bridges as 'turn-on' fluoride sensors”, Journal of the Chemical Society. Dalton Transactions, vol. 41, 2012, pp. 10328-10346.
Weber, L., Eickhoff, D., Kahlert, J., Böhling, L., Brockhinke, A., Stammler, H.-G., Neumann, B., Fox, M.A.: Diazaborolyl-boryl push-pull systems with ethynylene-arylene bridges as 'turn-on' fluoride sensors. Journal of the Chemical Society. Dalton Transactions. 41, 10328-10346 (2012).
Weber, Lothar, Eickhoff, Daniel, Kahlert, Jan, Böhling, Lena, Brockhinke, Andreas, Stammler, Hans-Georg, Neumann, Beate, and Fox, Mark A. “Diazaborolyl-boryl push-pull systems with ethynylene-arylene bridges as 'turn-on' fluoride sensors”. Journal of the Chemical Society. Dalton Transactions 41.34 (2012): 10328-10346.
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