1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence

Weber L, Werner V, Domke I, Stammler H-G, Neumann B (2006)
Journal of the Chemical Society. Dalton Transactions (31): 3777-3784.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
Reaction of 2-bromo-1,3-diethyl-1,3,2-benzodiazaborole (1) with equimolar amounts of thienyl lithium or 2,2'-dithienyl lithium led to the generation of benzodiazaboroles 2 and 3 which are functionalized at the boron atom by a 2-thienyl or a 5-(2,2'-dithienyl) unit. Similarly 2-bromo-1,3-diethyl-1,3,2-naphthodiazaborole (4) and thienyl lithium or 2,2'-dithienyl lithium afforded the naphthoborolyl-substituted thiophene 5 or dithiophene 6. Treatment of 2,5-bis(dibromoboryl)-thiophene 7 with 2 eq. of tBuN=CH-CH=NtBu in n-hexane followed by sodium amalgam reduction of the obtained bis(diazaborolium) salt 8 gave the 2,5- bis(diazaborolyl) thiophene 9. The 2,5-bis(diazaborolidinyl)-thiophene 10 resulted from the cyclocondensation of 7 with 2 eq. of N, N'-di-tert-butylethylenediamine in the presence of NEt3. Analogously, cyclocondensation of 7 with N, N'-diethylphenylenediamine gave the bis(benzodiazaborolyl) functionalized thiophene 11. The novel compounds were characterized by elemental analysis and spectroscopy (H-1-, B-11-, C-13-NMR, MS and UV-VIS). The molecular structure of 3 was elucidated by X-ray diffraction. Cyclovoltammograms show an irreversible oxidation wave at 298-598 vs. Fc/Fc(+). The borolylated thiophenes and dithienyls show intense blue luminescence with Stokes shifts of 30-107 nm.
Erscheinungsjahr
Zeitschriftentitel
Journal of the Chemical Society. Dalton Transactions
Ausgabe
31
Seite(n)
3777-3784
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Weber L, Werner V, Domke I, Stammler H-G, Neumann B. 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions. 2006;(31):3777-3784.
Weber, L., Werner, V., Domke, I., Stammler, H. - G., & Neumann, B. (2006). 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions(31), 3777-3784. doi:10.1039/b603365b
Weber, L., Werner, V., Domke, I., Stammler, H. - G., and Neumann, B. (2006). 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions, 3777-3784.
Weber, L., et al., 2006. 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions, (31), p 3777-3784.
L. Weber, et al., “1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence”, Journal of the Chemical Society. Dalton Transactions, 2006, pp. 3777-3784.
Weber, L., Werner, V., Domke, I., Stammler, H.-G., Neumann, B.: 1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence. Journal of the Chemical Society. Dalton Transactions. 3777-3784 (2006).
Weber, Lothar, Werner, Vanessa, Domke, Imme, Stammler, Hans-Georg, and Neumann, Beate. “1,3,2-Diazaborolyl-functionalized thiophenes and dithiophenes: synthesis, structure, electrochemistry and luminescence”. Journal of the Chemical Society. Dalton Transactions 31 (2006): 3777-3784.

3 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Triarylborane substituted naphthalimide as a fluoride and cyanide ion sensor.
Sheshashena Reddy T, Maragani R, Misra R., Dalton Trans 45(6), 2016
PMID: 26727393
Experimental and theoretical studies on organic D-π-A systems containing three-coordinate boron moieties as both π-donor and π-acceptor.
Weber L, Eickhoff D, Marder TB, Fox MA, Low PJ, Dwyer AD, Tozer DJ, Schwedler S, Brockhinke A, Stammler HG, Neumann B., Chemistry 18(5), 2012
PMID: 22213064
Luminescence properties of C-diazaborolyl-ortho-carboranes as donor-acceptor systems.
Weber L, Kahlert J, Brockhinke R, Böhling L, Brockhinke A, Stammler HG, Neumann B, Harder RA, Fox MA., Chemistry 18(27), 2012
PMID: 22623079

22 References

Daten bereitgestellt von Europe PubMed Central.


Entwistle, Angew. Chem. 114(), 2002

Entwistle, Chem. Mater. 16(), 2004

Doi, Chem. Mater. 15(), 2003

Charlot, PhysChemPhys 7(), 2005

Maruyama, J. Mater. Chem. 12(), 2002

Weber, Coord. Chem. Rev. 215(), 2001

Weber, Organometallics 24(), 2005

Weber, Eur. J. Inorg. Chem. (), 2005

Weber, Z. Anorg. Allg. Chem. 627(), 2001

Kuznetsova, Khim. Geterotsikl. Soedin. (), 1991

Niedenzu, Z. Anorg. Allg. Chem. 406(), 1976

Merriam, J. Organomet. Chem. 51(), 1973

Weber, Dalton Trans. (), 2004

Weber, Dalton Trans. (), 2006

Haberecht, Z. Anorg. Allg. Chem. 630(), 2004

Weber, Eur. J. Inorg. Chem. (), 1998

Weber, Eur. J. Inorg. Chem. (), 1999

Weber, Z. Naturforsch., B: Chem. Sci. 54(), 1999

Schmid, Inorg. Chem. 29(), 1990

Weber, Chem. Ber. 130(), 1997

Schmid, Angew. Chem. 103(), 1991

Hudson, J. Organomet. Chem. 637?639(), 2001

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