Please use this identifier to cite or link to this item:
Title: Head-to-tail regioregular oligothiophene-functionalized 9,9′-spirobifluorene derivatives. 1. Synthesis
Authors: Pei, J. 
Ni, J.
Zhou, X.-H.
Cao, X.-Y.
Lai, Y.-H. 
Issue Date: 12-Jul-2002
Citation: Pei, J., Ni, J., Zhou, X.-H., Cao, X.-Y., Lai, Y.-H. (2002-07-12). Head-to-tail regioregular oligothiophene-functionalized 9,9′-spirobifluorene derivatives. 1. Synthesis. Journal of Organic Chemistry 67 (14) : 4924-4936. ScholarBank@NUS Repository.
Abstract: Two series of novel fully conjugated oligomers, oligothiophene-functionalized 9,9′-spirobifluorene derivatives, have been developed in this contribution. First, four 9,9′-spirobifluorene bromide derivatives (compounds 1a-d) are prepared through various synthetic routes. Oligothiophene derivatives with or without substituents are synthesized through the Grignard and Suzuki coupling reactions. The Negishi coupling reactions between oligothienylzinc chloride and various 9,9′spirobifluorene bromides with Pd(PPh3)4 as catalyst successfully produce the desired compounds, unsubstituted oligothiophene-functionalized 9,9′-spirobifluorene derivatives, compounds 2 to 4ad. Since the Negishi coupling reactions afford regioregularly head-to-tail (H-T) oligo(4-nhexylthiophene)-functionalized 9,9′-spirobifluorene derivatives in poor yields, the Suzuki coupling reactions between sodium 4-n-hexylthienyl-2-boronate 8, and various 9,9′-spirobifluorene-based bromides 1a-d and 9-16 are employed to produce highly regioregular head-to-tail oligothiophenefunctionalized 9,9′-spirobifluorene derivatives (compounds 5 to 7a-d) in very high yields. We also investigate the effect of solvents on the Suzuki coupling reactions. The structure and purity of all compounds are verified by FT-IR, 1H and 13C NMR, MS, and elemental analysis.
Source Title: Journal of Organic Chemistry
ISSN: 00223263
DOI: 10.1021/jo011146z
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.


checked on Mar 25, 2020


checked on Mar 25, 2020

Page view(s)

checked on Mar 15, 2020

Google ScholarTM



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.