Self-assembly of a novel series of hetero-duplexes driven by donor-acceptor interaction |
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Authors: | Qi-Zhong Zhou Xue-Bin Shao Xi-Kui Jiang Guang-Ju Chen |
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Affiliation: | a State Key Laboratory of Bio-Organic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China b Department of Chemistry, Beijing Normal University, Beijing 100875, China c Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100101, China |
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Abstract: | The self-assembly of a novel series of donor-acceptor interaction-driven artificial hetero-duplexes in organic media has been described. Four linear compounds 1a-1d, bearing two to five electron rich 1,5-dioxynaphthalene units connected by the tetra(ethylene glycol) linker, respectively, have been prepared and used as donors, while eight compounds 2a-2d, 13-16, bearing one to four electron deficient pyromellitic diimide, 1,4,5,8-naphthalene-tetracarboxydiimide, or perylene-3,4,9,10-tetracarboxydiimide units, respectively, have been used as acceptors. The structure of the hetero-duplexes has been characterized by the 1H NMR, UV-vis spectroscopy and vapor pressure osmometry. It is revealed that the binding stability of the duplexes vary greatly, depending on the length and structure of the monomers and also the solvent, and hetero-duplex 1d·2d displays a maximum association constant of ca. 1.0×104 M−1 in chloroform. |
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Keywords: | Self-assembly Donor-acceptor interaction Aromatic stacking Dimer Oligo(glycol) |
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