Synthesis and physical properties of [4]cyclo-3,7-dibenzo[b,d]thiophene and its S,S-dioxide

作者: Eiichi Kayahara , Xue Zhai , Shigeru Yamago

DOI: 10.1139/CJC-2016-0474

关键词:

摘要: Cyclic tetramers of 3,7-dibenzo[b,d]thiophene (DBT) and 3,7-dibenzo[b,d]thiophene-5,5-dioxide (DBTO), i.e., [4]cyclo-DBT ([4]CDBT) [4]cyclo-DBTO ([4]CDBTO), respectively, are synthesized by the platinum-mediated assembly bis-metallated DBT DBTO subsequent reductive elimination platinum. This is first example synthesis sulfur-containing cycloparaphenylene (CPP) derivatives. The structure [4]CDBTO unambiguously determined single crystal X-ray analysis. Theoretical experimental analyses their physical properties reveal effect sulfur atom sulfonyl group at periphery biphenyl units CPP.

参考文章(63)
William R. Cullen, Tae Jeong Kim, Frederick W. B. Einstein, Terry Jones, Structure of the hydrogenation catalyst [(PP)Rh(NBD)]ClO4, PP = (.eta.5-(Me3C)2PC5H4)2Fe, and some comparative rate studies Organometallics. ,vol. 2, pp. 714- 719 ,(1983) , 10.1021/OM00078A004
Shigeru Yamago, Yoshiki Watanabe, Takahiro Iwamoto, Synthesis of [8]cycloparaphenylene from a square-shaped tetranuclear platinum complex. Angewandte Chemie. ,vol. 49, pp. 757- 759 ,(2010) , 10.1002/ANIE.200905659
Eiichi Kayahara, Takahiro Iwamoto, Toshiyasu Suzuki, Shigeru Yamago, Selective Synthesis of [6]-, [8]-, and [10]Cycloparaphenylenes Chemistry Letters. ,vol. 42, pp. 621- 623 ,(2013) , 10.1246/CL.130188
Ramesh Jasti, Joydeep Bhattacharjee, Jeffrey B. Neaton, Carolyn R. Bertozzi, Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cycloparaphenylene: Carbon Nanohoop Structures Journal of the American Chemical Society. ,vol. 130, pp. 17646- 17647 ,(2008) , 10.1021/JA807126U
Kazukuni Tahara, Yoshito Tobe, Molecular loops and belts. Chemical Reviews. ,vol. 106, pp. 5274- 5290 ,(2006) , 10.1021/CR050556A
Kengo Asai, Aiko Fukazawa, Shigehiro Yamaguchi, A cyclic octithiophene containing β,β′-linkages Chemical Communications. ,vol. 51, pp. 6096- 6099 ,(2015) , 10.1039/C5CC00570A
Hua-Wei Jiang, Takayuki Tanaka, Hirotaka Mori, Kyu Hyung Park, Dongho Kim, Atsuhiro Osuka, Cyclic 2,12-Porphyrinylene Nanorings as a Porphyrin Analogue of Cycloparaphenylenes Journal of the American Chemical Society. ,vol. 137, pp. 2219- 2222 ,(2015) , 10.1021/JA513102M
Shigeru Yamago, Tetsuro Majima, Mamoru Fujitsuka, Sachiko Tojo, Takahiro Iwamoto, Eiichi Kayahara, Radical Ions of Cycloparaphenylenes: Size Dependence Contrary to the Neutral Molecules. Journal of Physical Chemistry Letters. ,vol. 5, pp. 2302- 2305 ,(2014) , 10.1021/JZ5009054
Takahiro Iwamoto, Zdenek Slanina, Naomi Mizorogi, Jingdong Guo, Takeshi Akasaka, Shigeru Nagase, Hikaru Takaya, Nobuhiro Yasuda, Tatsuhisa Kato, Shigeru Yamago, Partial Charge Transfer in the Shortest Possible Metallofullerene Peapod, La@C82⊂[11]Cycloparaphenylene Chemistry: A European Journal. ,vol. 20, pp. 14403- 14409 ,(2014) , 10.1002/CHEM.201403879
Takahiro Iwamoto, Eiichi Kayahara, Nobuhiro Yasuda, Toshiyasu Suzuki, Shigeru Yamago, Synthesis, characterization, and properties of [4]cyclo-2,7-pyrenylene: effects of cyclic structure on the electronic properties of pyrene oligomers. Angewandte Chemie. ,vol. 53, pp. 6430- 6434 ,(2014) , 10.1002/ANIE.201403624