NDLI: Diazaborolyl-boryl push–pull systems with ethynylene–arylene bridges as ‘turn-on’ fluoride sensors

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Stammler, Hans-georg Fox, Mark A. Kahlert, Jan Eickhoff, Daniel Weber, Lothar Brockhinke, Andreas Neumann, Beate Böhling, Lena
Description	Author Affiliation: Weber L ( Fakultät für Chemie der Universität Bielefeld, 33615 Bielefeld, Germany. lothar.weber@uni-bielefeld.de)
Abstract	Two linear π-conjugated systems with 1,3-diethyl-1,3,2-benzodiazaborolyl $[C_{6}H_{4}(NEt)_{2}B–]$ as a donor group and dimesitylboryl $(–BMes_{2})$ as acceptor were synthesised with –ethynylene–phenylene- $(–C\&\#8801;C-1,4-C_{6}H_{4}–,$ 3) and –ethynylene–thiophene– $(–C\&\#8801;C-2,5-C_{4}H_{2}S–$ 12) bridges between the boron atoms. An assembly (20) consisting of two diazaborolyl-ethynylene–phenylene-boryl units, $[C_{6}H_{4}(NCy)(N′)B–C\&\#8801;C-1,4-C_{6}H_{4}-BMes_{2}]$ 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 $(NBu_{4})(12·F)$ were elucidated by X-ray diffraction analyses. The borylated systems 3, 12 and 20 show intense blue luminescence in cyclohexane with quantum yields $(Φ_{fl})$ of 0.99, 0.44 and 0.94, respectively, but weak blue-green luminescence in tetrahydrofuran $(Φ_{fl}$ = 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.
ISSN	14779226
Issue Number	34
Journal	Dalton Trans.
Volume Number	41
e-ISSN	13645447
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2012-09-14
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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