Use of Stable Amine-Capped Polyynes in the Regioselective Synthesis of Push–Pull Thiophenes
作者： Bartłomiej Pigulski , Patrycja Męcik , Jakub Cichos , Sławomir Szafert
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摘要: The reactions of a series 1-halopolyynes with secondary amines led to novel amine end-capped polyynes exhibiting surprisingly high stability toward moisture. new compounds were characterized by NMR spectroscopy, ESI-MS spectrometry, and X-ray single-crystal diffractometry. use as precursors substituted push–pull thiophenes was next presented. results show the first—to best our knowledge—transformation ynamine thiophene first regioselective transformation longer butadiyne-substituted thiophene. Photophysical studies resulting that some have quantum yield photoluminescence upon UV light irradiation.
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sci-hub.se 参考文章(79)
Rik R. Tykwinski, Carbyne: The Molecular Approach. Chemical Record. ,vol. 15, pp. 1060- 1074 ,(2015) , 10.1002/TCR.201500018
François Diederich, Peter J Stang, Rik R Tykwinski, Acetylene chemistry : chemistry, biology and material science Wiley-VCH. ,(2004) , 10.1002/3527605487
Hiroyuki Watanabe, Masahiro Ono, Hideo Saji, In vivo fluorescence imaging of β-amyloid plaques with push–pull dimethylaminothiophene derivatives Chemical Communications. ,vol. 51, pp. 17124- 17127 ,(2015) , 10.1039/C5CC06628J
Juliette Collard-Motte, Zdenek Janousek, Synthesis of ynamines Topics in Current Chemistry. ,vol. 130, pp. 89- 131 ,(1986) , 10.1007/3-540-15810-3_3
Hongjian Jin, Christopher N. Young, Gary P. Halada, Brian L. Phillips, Nancy S. Goroff, Synthesis of the Stable Ordered Conjugated Polymer Poly(dibromodiacetylene) from an Explosive Monomer Angewandte Chemie International Edition. ,vol. 54, pp. 14690- 14695 ,(2015) , 10.1002/ANIE.201504713
Denis N. Tomilin, Bartłomiej Pigulski, Nurbey Gulia, Agata Arendt, Lyubov N. Sobenina, Al'bina I. Mikhaleva, Sławomir Szafert, Boris A. Trofimov, Direct synthesis of butadiynyl-substituted pyrroles under solvent- and transition metal-free conditions RSC Advances. ,vol. 5, pp. 73241- 73248 ,(2015) , 10.1039/C5RA08820H
Aiwu Sun, Joseph W Lauher, Nancy S Goroff, Preparation of Poly(diiododiacetylene), an Ordered Conjugated Polymer of Carbon and Iodine Science. ,vol. 312, pp. 1030- 1034 ,(2006) , 10.1126/SCIENCE.1124621
Yui Tokutome, Tsunehisa Okuno, Preparations, crystal polymorphs and DFT calculations of N1,N1,N4,N4-tetraphenylbuta-1,3-diyne-1,4-diamine Journal of Molecular Structure. ,vol. 1047, pp. 136- 142 ,(2013) , 10.1016/J.MOLSTRUC.2013.05.013
Bernhard Witulski, Torsten Schweikert, Dieter Schollmeyer, Nicolai A. Nemkovich, Synthesis and molecular properties of donor–π-spacer–acceptor ynamides with up to four conjugated alkyne units Chemical Communications. ,vol. 46, pp. 2953- 2955 ,(2010) , 10.1039/B919275A
Slawomir Szafert, J. A. Gladysz, Carbon in one dimension: structural analysis of the higher conjugated polyynes. Chemical Reviews. ,vol. 103, pp. 4175- 4205 ,(2003) , 10.1021/CR030041O