A Coformer Approach for Supramolecular Polymerization at High Concentrations |
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Authors: | Atsushi Isobe Dr Takashi Kajitani Prof Dr Shiki Yagai |
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Institution: | 1. Division of Advanced Science and Engineering, Graduate School of Science and Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, 263-8522 Chiba, Japan;2. TC College Promotion Office, Open Facility Center, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, 226-8503 Yokohama, Japan;3. Institute for Advanced Academic Research (IAAR), Chiba University, 1-33 Yayoi-cho, Inage-ku, 263-8522 Chiba, Japan |
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Abstract: | Insolubility of functional molecules caused by polymorphism sometimes poses limitations for their solution-based processing. Such a situation can also occur in the preparation processes of supramolecular polymers formed in a solution. An effective strategy to address this issue is to prepare amorphous solid states by introducing a “coformer” molecule capable of inhibiting the formation of an insoluble polymorph through co-aggregation. Herein, inspired by the coformer approach, we demonstrated a solubility enhancement of a barbiturate π-conjugated compound that can supramolecularly polymerize through six-membered hydrogen-bonded rosettes. Our newly synthesized supramolecular coformer molecule features a sterically demanding methyl group in the π-conjugated unit of the parent molecule. Although the parent molecule exhibits low solubility in nonpolar solvents due to the formation of a crystalline polymorph comprising a tape-like hydrogen-bonded array prior to the supramolecular polymerization, mixing with the coformer compound enhanced the solubility by inhibiting mesoscopic organization of the tapes. The two monomers were then co-polymerized into desired helicoidal supramolecular polymers through the formation of heteromeric rosettes. |
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Keywords: | Barbituric Acid Co-Assembly Coformer Polymorphism Supramolecular Polymer |
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