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Synfacts 2010(2): 0165-0165  
DOI: 10.1055/s-0029-1219074
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

An Insulated Conjugated Polymer Wire

Contributor(s):Timothy M. Swager, Jan M. Schnorr
J. Terao*, S. Tsuda, Y. Tanaka, K. Okoshi*, T. Fujihara, Y. Tsuji, N. Kambe*
Kyoto University, PRESTO, Japan Science and Technology Agency, Kyoto, Osaka University and Tokyo Institute of Technology, Japan
Synthesis of Organic-Soluble Conjugated Polyrotaxanes by Polymerization of Linked Rotaxanes
J. Am. Chem. Soc.  2009,  131:  16004-16005  
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Publication History

Publication Date:
21 January 2010 (online)

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Key words

polyrotaxanes - host-guest systems - conjugated polymers

Significance

Insulated molecular wires are an interesting target for molecular electronics. The authors synthesize such a structure (5) by polymerizing 4, in which a conjugated unit is surrounded by a permethylated α-cyclodextrin (PM α-CD). Intermediate 3 is obtained using a recently reported route (S. Tsuda, J. Terao, N. Kambe Chem. Lett. 2009, 38, 76).

Comment

Polymer 6 containing repeat units with two PM α-CD moieties was synthesized using the same strategy. Compared to the equivalent in which PM α-CD units are attached at the same positions but not including the conjugated system through a host-guest pair, it shows a significantly higher solid-state quantum yield (23% vs. 6%). This suggests shielding of the molecular wire in 6.

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