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Complex Formation of Cyclodextrins with Various Thiophenes and their Polymerization in Water: Preparation of Poly-pseudo-rotaxanes containing Poly(thiophene)s

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Abstract

Cyclodextrins (α-CD, β-CD and 2,6-di-O-dimethyl-β-CD (DM-β-CD)) were found to form inclusion compounds with thiophenes (thiophene (T), bithiophene (2T)) in water and in crystalline states. The structures of α-CD–T, β-CD–2T, and DM-β-CD–2T inclusion complexes were determined by X-ray crystallography. DM-β-CD forms a 1:1 cage type complex with 2T. In contrast, β-CD formed 2:3 (CD:guest) complexes with thiophene and α-CD formed 2:3 complexes, both of the channel type. These inclusion complexes were found to polymerize by FeCl3 in the inclusion compounds in water. The products were formed poly-pseudo-rotaxane between cyclodextrins and poly(thiophene) characterized by IR, 1H-NMR and 13C CP/MAS NMR. The molecular weights of the poly-pseudo-rotaxanes with poly(thiophene) were determined by the MALDI-TOF mass spectra to be 3000–5000. In comparison between poly-pseudo-rotaxane (DM-β-CD–poly(thiophene)), authentic poly(thiophene) and the washed DM-β-CD–poly(thiophene) which was washed with DMF to dethread DM-β-CD, these poly-pseudo-rotaxane was characterized by Raman, UV–vis and fluorescence spectra. The maximum emission band of DM-β-CD–poly(thiophene) shifted to a shorter wavelength. The hypsochromic shift was derived from poly-pseudo-rotaxane with DM-β-CD.

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Acknowledgements

This work has been partially supported by Grant in-Aid No. S14103015 for Scientific Research and has been conducted with financial support from the 21st Century Center of Excellence (COE) program of the Ministry of Education, Culture, Sports, Science and Technology, Japan.

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Authors and Affiliations

  1. Department of Macromolecular Science, Graduate School of Science, Osaka University, 560-0043, Toyonaka, Osaka, Japan

    YOSHINORI TAKASHIMA, KAZUYA SAKAMOTO, YOSHIFUMI OIZUMI, HIROYASU YAMAGUCHI & AKIRA HARADA

  2. Information Technology Center Kagawa University, Kagawa, Japan

    SHIGEHIRO KAMITORI

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  1. YOSHINORI TAKASHIMA
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  2. KAZUYA SAKAMOTO
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Correspondence to AKIRA HARADA.

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TAKASHIMA, Y., SAKAMOTO, K., OIZUMI, Y. et al. Complex Formation of Cyclodextrins with Various Thiophenes and their Polymerization in Water: Preparation of Poly-pseudo-rotaxanes containing Poly(thiophene)s. J Incl Phenom Macrocycl Chem 56, 45–53 (2006). https://doi.org/10.1007/s10847-006-9059-4

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