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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Abstract
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.
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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.
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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On the ambiguity of 1,3,2-benzodiazaboroles as donor/acceptor functionalities in luminescent molecules.
Weber L, Halama J, Hanke K, Bohling L, Brockhinke A, Stammler HG, Neumann B, Fox MA., Dalton Trans 43(8), 2014
PMID: 24366446

120 References

Data provided by Europe PubMed Central.


Codding, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. B34(), 1978

Codding, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. B35(), 1979

Baenziger, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. B32(), 1976

El, Transition Met. Chem. 22(), 1997
Quenching of a photosensitized dye through single-electron transfer from trivalent phosphorus compounds
Yasui S, Tsujimoto M, Itoh K, Ohno A., J. Org. Chem. 65(15), 2000
PMID: 10959880

Yamagushi, J. Organomet. Chem. 646(), 2002

Abe, Inorg. Chem. 37(), 1998

Kobayashi, Chem. Phys. Lett. 420(), 2006

Jacquemin, J. Chem. Phys. 14(), 2007

Becke, J. Chem. Phys. 98(), 1993
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.
Lee C, Yang W, Parr RG., Phys. Rev., B Condens. Matter 37(2), 1988
PMID: 9944570

Joant??guy, J. Phys. Chem. B: J. Phys. Chem. 103(), 1999
Gas-Phase Generation and Photoelectron Spectra of Reactive Unsubstituted Cycloalkenethiones.
Chrostowska A, Miqueu K, Pfister-Guillouzo G, Briard E, Levillain J, Ripoll JL., J Mol Spectrosc 205(2), 2001
PMID: 11162220

Bartnik, Eur. J. Org. Chem. (), 2003

Stratmann, J. Chem. Phys. 109(), 1998

Casida, J. Chem. Phys. 108(), 1998
Calculation of ionization potentials of small molecules: a comparative study of different methods.
Lemierre V, Chrostowska A, Dargelos A, Chermette H., J Phys Chem A 109(37), 2005
PMID: 16834226

Sheldrick, Acta Crystallogr., Sect. A: Fundam. Crystallogr. A46(), 2008

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