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Head-to-tail Regioregular Oligothiophene-Functionalized 9,9'-spirobifluorene Derivatives. 1. Synthesis

Head-to-tail Regioregular Oligothiophene-Functionalized 9,9'-spirobifluorene Derivatives. 1. Synthesis

Jian Pei, Jing Ni, Xing-Hua Zhou, Xiao-Yu Cao, Yee-Hing Lai

J Org Chem. 2002 Jul 12;67(14):4924-36.

PMID: 12098307

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(PPh(3))(4) as catalyst successfully produce the desired compounds, unsubstituted oligothiophene-functionalized 9,9'-spirobifluorene derivatives, compounds 2 to 4a-d. Since the Negishi coupling reactions afford regioregularly head-to-tail (H-T) oligo(4-n-hexylthiophene)-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 oligothiophene-functionalized 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, (1)H and (13)C NMR, MS, and elemental analysis.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP159660	9,9′-Spirobifluorene		159-66-0	Price

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