DOI: 10.1246/bcsj.62.1539. Novel Electron Acceptors Bearing a Heteroquinonoid System. I. Synthesis and Conductive Complexes of 5,5′-Bis(dicyanomethylene)-5,5′-dihydro-<i>Δ</i>2,2′-bithiophene and Related Compounds

Novel Electron Acceptors Bearing a Heteroquinonoid System. I. Synthesis and Conductive Complexes of 5,5′-Bis(dicyanomethylene)-5,5′-dihydro-Δ2,2′-bithiophene and Related Compounds

10.1246/bcsj.62.1539

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract Novel electron acceptors bearing a heteroquinonoid system, 5,5′-bis(dicyanomethylene)-5,5′-dihydro-Δ2,2′-bithiophene, its 3,3′-dichloro, 3,3′-dibromo, and 3,3′,4,4′-tetrabromo derivatives, and 5,5″-bis(dicyanomethylene)5,5″-dihydro-Δ2,2′:5′,2″-terthiophene were synthesized by the action of tetracyanoethylene oxide or by Pd(0)-catalyzed substitution reactions with sodium dicyanomethanide on the corresponding α,α′-dihalogenoheteroaromatics. They showed very small on-site Coulomb repulsion as expected, and afforded several highly conductive molecular complexes with electron donors such as hexamethylenetetratellurafulvalene.

Bibliography

Yui, K., Aso, Y., Otsubo, T., & Ogura, F. (1989). Novel Electron Acceptors Bearing a Heteroquinonoid System. I. Synthesis and Conductive Complexes of 5,5â²-Bis(dicyanomethylene)-5,5â²-dihydro-Î2,2â²-bithiophene and Related Compounds. Bulletin of the Chemical Society of Japan, 62(5), 1539â1546.

Authors 4

Koji Yui (first)
Yoshio Aso (additional)
Tetsuo Otsubo (additional)
Fumio Ogura (additional)

References 41 Referenced 99

10.1021/jo00909a019
10.1021/ja00429a030
{'key': '2024011814280210500_r3'}
10.1021/ar50135a001
10.1038/309119a0
{'key': '2024011814280210500_r6'}
{'key': '2024011814280210500_r7'}
{'key': '2024011814280210500_r8'}
10.1021/jo00345a024
10.1021/jo00211a001
{'key': '2024011814280210500_r11'}
10.1021/jo00922a035
10.1246/bcsj.52.3739
{'key': '2024011814280210500_r14'}
10.1021/j100441a017
{'key': '2024011814280210500_r16'}
10.1021/jo01254a019
10.1246/bcsj.43.1411
10.3891/acta.chem.scand.15-1393
{'key': '2024011814280210500_r20'}
10.1093/jee/78.1.121
10.1016/S0040-4020(01)96555-X
10.3987/R-1985-08-1907
10.1016/S0040-4039(00)88257-X
{'key': '2024011814280210500_r25'}
10.1016/S0040-4039(00)98550-2
10.1016/S0040-4039(00)89262-X
{'key': '2024011814280210500_r28'}
10.1246/bcsj.60.3163
10.1021/ja00399a066
10.1021/jo00930a043
{'key': '2024011814280210500_r32'}
10.1021/jo00866a041
10.1021/jo01338a048
10.1080/00268948408072069
10.1246/bcsj.61.2013
10.1002/jlac.19375270119
10.1002/jlac.19405430111
{'key': '2024011814280210500_r39'}
10.1002/jlac.19415460112
10.1021/ja01194a031

Dates

Type	When
Created	19 years, 1 month ago (July 25, 2006, 9:59 p.m.)
Deposited	1 year, 7 months ago (Jan. 18, 2024, 9:28 a.m.)
Indexed	53 minutes ago (Sept. 2, 2025, 9:57 p.m.)
Issued	36 years, 4 months ago (May 1, 1989)
Published	36 years, 4 months ago (May 1, 1989)
Published Online	19 years, 2 months ago (June 27, 2006)
Published Print	36 years, 4 months ago (May 1, 1989)

Funders 0

None

BibTeX

@article{Yui_1989, title={Novel Electron Acceptors Bearing a Heteroquinonoid System. I. Synthesis and Conductive Complexes of 5,5′-Bis(dicyanomethylene)-5,5′-dihydro-Δ2,2′-bithiophene and Related Compounds}, volume={62}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.62.1539}, DOI={10.1246/bcsj.62.1539}, number={5}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Yui, Koji and Aso, Yoshio and Otsubo, Tetsuo and Ogura, Fumio}, year={1989}, month=may, pages={1539–1546} }

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