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Bolaamphiphiles Bearing Bipyridine as Mesogenic Core: Rational Exploitation of Molecular Architectures for Controlled Self-Assembly

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Key Lab of Organic Optoelectronics & Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China
Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium
§ School of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.
*Fax: (+86) 10-6277-1149; e-mail: [email protected]
Cite this: Langmuir 2012, 28, 11, 5023–5030
Publication Date (Web):March 9, 2012
https://doi.org/10.1021/la300369w
Copyright © 2012 American Chemical Society
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Abstract

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A bolaamphiphile (5,5-B2NBr8) bearing a functional bipyridine moiety as the mesogenic core is reported for the first time. 5,5-B2NBr8 was found to self-assemble into uniform fibrous structure in aqueous solution, when the concentration was higher than cmc. Analogues of 5,5-B2NBr8 with structural differences in chain length, headgroup, mesogenic core, and substituted position were synthesized, elucidating that small variances of the molecular structure could lead to dramatic changes of the resulting assemblies. For example, compound 4,4-B2NBr8 showed only spherical colloidal aggregates rather than fibers as 5,5-B2NBr8 did, while the only difference between them was the position at which the alkyl chains were attached onto bipyridine. A probable model for the fibrous structure of 5,5-B2NBr8 was proposed. Moreover, exploiting the coordination capacity of bipyridine, assembly and disassembly of 5,5-B2NBr8 could be reversibly controlled through the addition of EDTA and Cu(II), respectively.

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Cmc measurement, concentration-dependent assembly of 5,5-B2NBr8, section analysis of AFM images, AFM and TEM images of analogues, structure optimization through DFT:B3LYP/6-31g** basis set, elaboration on the assembly of 4,4-B2NBr8, binding constant measurement, details of single-crystal X-ray experiment, and details of synthesis including NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org.

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