Self-assembly of a new series of quadruply hydrogen bonded heterotrimers driven by the donor-acceptor interaction |
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Authors: | Xiao-Qiang Li Xiao-Zhong Wang Zhan-Ting Li Guang-Ju Chen Yi-Hua Yu |
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Institution: | 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 School of Science and Engineering, East China Normal University, Shanghai 200062, China |
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Abstract: | This paper describes the self-assembly of a new series of heterotrimers in chloroform-d by utilizing the cooperative interaction of hydrogen bonding and donor-acceptor interaction. Compounds 1 and 11, in which an 2-ureido-41H]-pyrimidinone unit is connected to 34-crown-10 or 36-crown-10, were used as donor monomer, and 2 and 19, in which an 2-ureido-41H]-pyrimidinone unit is connected to NDI, were used as acceptor monomer, while linear compound 4, which contains two diamido-1,8-naphthyridines, was used as template. A large tri-p-(t-butyl)phenylmethoxyl group was introduced to 19 in order to compare its assembling behavior with that of 2. Mixing 4 with dimer 1·2 caused 1·2 to fully decompose and to afford 55% of ‘in-in’-oriented heterotrimer 1·4·2. Adding 4 to the solution of 2·11 or 11·19 in chloroform-d also led to full dissociation of the dimers. However, in these systems the ‘in-in’-arranged heterotrimer 2·4·11 or 11·4·19 could be produced exclusively. |
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Keywords: | Hydrogen bonding Donor-acceptor interaction Self-assembly Heterocycle Supramolecular chemistry |
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