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Synthesis and X-Ray Crystal and Molecular Structure of1,6-Bis(3-thienyl)hexane

 

作者: Penny A. Chaloner,  

 

期刊: Journal of Chemical Research, Synopses  (RSC Available online 1997)
卷期: Volume 0, issue 8  

页码: 267-267

 

ISSN:0308-2342

 

年代: 1997

 

DOI:10.1039/a607896f

 

出版商: RSC

 

数据来源: RSC

 

摘要:

S S 1 J. CHEM. RESEARCH (S), 1997 267 J. Chem. Research (S), 1997, 267 J. Chem. Research (M), 1997, 1882–1888 Synthesis and X-Ray Crystal and Molecular Structure of 1,6-Bis(3-thienyl)hexane Penny A. Chaloner,* Sumudu R. Gunatunga and Peter B. Hitchcock School of Chemistry, Physics and Environmental Science, University of Sussex, Falmer, Brighton BN1 9QJ, UK 1,6-Bis(3-thienyl)hexane has been prepared and characterised in an X-ray diffraction study. There is considerable interest in polythiophenes and oligothiophenes because they are conducting when doped and may be used for third harmonic generation.1 We report here that 1,6-bis(3-thienyl)hexane (1) is prepared by the coupling of 1,6-bis(bromomagnesiohexane) with 3-bromothiophene in the presence of [NiCl2(dppp)],14† the product being isolated by distillation followed by low temperature recrystallisation. It did not prove possible to cyclise 1 under oxidative conditions using palladium(II).16 Bromination of 1 (NBS–DMF†,17) gave 1,6-bis(2-bromo-3-thienyl)hexane in reasonable yield, but successful cyclisation of the bromo compound also proved elusive.The structure of 1 was determined (direct methods, SHELXS-86, SHELXL-93, R1=0.070, wR2=0.175) by X-ray crystallography (Fig. 1); the molecule lies across a crystallographic inversion centre. The thiophene ring is planar and unstrained, and the molecular dimensions are similar to those in bithiophene.2 Techniques used: 1H and 13C NMR spectroscopy, X-ray diffraction References: 23 Fig. 2: Packing diagram for 1 Tables 1, 2: Atomic coordinates, bond lengths and angles for 1 Received, 21st November 1996; Accepted, 6th May 1997 Paper E/6/07896F References cited in this synopsis 1 J. Roncali, Chem. Rev., 1992, 92, 711. 2 P. A. Chaloner, S. R. Gunatunga and P. B. Hitchcock, Acta Crystallogr., Sect. C, 1994, 50, 1941. 14 K. Tamao, K. Sumitani and M. Kumada, J. Am. Chem. Soc., 1972, 94, 4374. 16 I. V. Kozhevnikov and K. I. Matveev, Russ. Chem. Rev., 1978, 47, 649. 17 P. Bauerle, F. Wurthner, G. Gotz and T. Effenberger, Synthesis, 1993, 1099. *To receive any correspondence. †Abbreviations used: dppp=1,3-(diphenylphosphino)propane; NBS=N-bromosuccinimide. Fig. 1 Structure of 1,6-bis(3-thienyl)hexane) (1). C14H18S2, M=250.4, monoclinic, a=5.960(2), b=17.952(7), c=6.629(2) Å, b=107.36(3)°, V=677.0(4) Å3, space group P21/n (nonstandard No. 14), Z=2, Dx=1.23 g cmµ3. R1=0.070, wR2=0.175. Selected bond lengths (Å) and angles (°): S–C(1) 1.704(4); S–C(4) 1.700(4); C(1)–C(2) 1.360(5); C(2)–C(3) 1.411(5); C(3)–C(4) 1.390(5) Å. C(1)–S–C(4) 92.7(2); S–C(1)–C(2) 113.1(3); C(1)–C(2)–C(3) 110.0(4); C(2)–C(3)–C(4) 114.9(4); S–C(4)–C(3) 109.2(3)

 



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