Topochemical polymerisation of assembled diacetylene macrocycle bearing dibenzylphosphine oxide in solid state |
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| Authors: | Xiaoning Zhang Chao Deng Meng Wang Xin Liu |
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| Affiliation: | Key Laboratory of Mesoscopic Chemistry of MOE, Center for Multimolecular Organic Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, P.R. China |
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| Abstract: | Novel diacetylene macrocycles 1 and 2 bearing dibenzylphosphine oxide were synthesised via Eglinton acetylenic intramolecular coupling. The X-ray analysis of crystals of macrocycles 1 and 2 demonstrated that the better-aligned tubular supramolecular structure was formed in macrocycle 1 than in macrocycle 2, which provided the possibility of diacetylene topochemical polymerisation in solid state of macrocycle 1. UV–vis, Raman spectroscopy and X-ray analysis indicated that the crystals of macrocycle 1 could undergo topochemical diacetylene polymerisation only on their surface by light irradiation; differential scanning calorimetry, solid-state 13C NMR spectroscopy and solubility test demonstrated that the crystals of macrocycle 1 could undergo diacetylene topochemical polymerisation inside solid by heat. As expected, based on the topological analysis of crystal structure, the crystals of macrocycle 2 could not undergo diacetylene topochemical polymerisation either by light irradiation or heat. |
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| Keywords: | Topochemical polymerisation supramolecular chemistry polydiacetylenes dibenzylphosphine oxide |
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