Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions

Weber L, Kuhtz H, Böhling L, Brockhinke A, Chrostowska A, Dargelos A, Maziere A, Stammler H-G, Neumann B (2012)
Journal of the Chemical Society. Dalton Transactions 41(34): 10440-10452.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
A series of 1,4-phenylenes X-C6H4-BDB with a 1,3,2-benzodiazaborolyl (BDB) and a phosphorus based end group [X = PPh2 (2), P(O)Ph-2 (3), P(S)Ph-2 (4), P(Se)Ph-2 (5), P(AuCl)Ph-2 (6) and P(Me)Ph-2 (7)] as well as 2-(2')thienyl-1,3,2-benzodiazaboroles with a second end group X [X = PPh2 (8), P(S)Ph-2 (9), P(Se)Ph-2 (10) and P(Me)Ph-2 (11)] in the 5' position were synthesised using established methodologies. Molecular structures of 2-9 and 11 were determined by X-ray diffraction. Compounds 3, 4, 6, 7, 9 and 11 show intense blue luminescence in cyclohexane, toluene, chloroform, dichloromethane and tetrahydrofuran with pronounced solvatochromism. Thereby Stokes shifts in the range of 8950-10 440 cm(-1) and quantum yields up to 0.70 were observed in dichloromethane solutions. In contrast to this, for the selenides 5 and 10 quantum yields are small (<0.1). The absorption maxima (298-340 nm) are well reproduced by TD-DFT computations (B3LYB/G-311G(d,p)) and arise from strong HOMO-LUMO transitions. With the exception of 5 and 10 the HOMOs of the molecules under study are mainly located on the benzodiazaborole group. In 5 and 10 the HOMOs are on the selenium atoms. The LUMOs of all new neutral molecules are mainly represented by the phenylene or thiophene bridge. In the phosphonium cations the LUMOs have additional contributions from the phosphonium unit.
Erscheinungsjahr
Zeitschriftentitel
Journal of the Chemical Society. Dalton Transactions
Band
41
Ausgabe
34
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10440-10452
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Weber L, Kuhtz H, Böhling L, et al. Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions. Journal of the Chemical Society. Dalton Transactions. 2012;41(34):10440-10452.
Weber, L., Kuhtz, H., Böhling, L., Brockhinke, A., Chrostowska, A., Dargelos, A., Maziere, A., et al. (2012). Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions. Journal of the Chemical Society. Dalton Transactions, 41(34), 10440-10452. doi:10.1039/c2dt30666b
Weber, L., Kuhtz, H., Böhling, L., Brockhinke, A., Chrostowska, A., Dargelos, A., Maziere, A., Stammler, H. - G., and Neumann, B. (2012). Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions. Journal of the Chemical Society. Dalton Transactions 41, 10440-10452.
Weber, L., et al., 2012. Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions. Journal of the Chemical Society. Dalton Transactions, 41(34), p 10440-10452.
L. Weber, et al., “Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions”, Journal of the Chemical Society. Dalton Transactions, vol. 41, 2012, pp. 10440-10452.
Weber, L., Kuhtz, H., Böhling, L., Brockhinke, A., Chrostowska, A., Dargelos, A., Maziere, A., Stammler, H.-G., Neumann, B.: Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions. Journal of the Chemical Society. Dalton Transactions. 41, 10440-10452 (2012).
Weber, Lothar, Kuhtz, Henry, Böhling, Lena, Brockhinke, Andreas, Chrostowska, Anna, Dargelos, Alain, Maziere, Audrey, Stammler, Hans-Georg, and Neumann, Beate. “Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions”. Journal of the Chemical Society. Dalton Transactions 41.34 (2012): 10440-10452.

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Triazaphospholenium Tetrafluoroborate: A Phosphorus Analogue of a 1,2,3-Triazole-Derived Carbene.
Papke M, Dettling L, Sklorz JAW, Szieberth D, Nyulászi L, Müller C., Angew Chem Int Ed Engl 56(52), 2017
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On the ambiguity of 1,3,2-benzodiazaboroles as donor/acceptor functionalities in luminescent molecules.
Weber L, Halama J, Hanke K, Böhling L, Brockhinke A, Stammler HG, Neumann B, Fox MA., Dalton Trans 43(8), 2014
PMID: 24366446

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