Multi-responsive rotaxane with tunable fluorescence under azobenzene-based benzoxazine structure

Sorapat NIYOMSIN; Suwabun CHIRACHANCHAI; Toshikazu TAKATA

doi:10.55713/jmmm.v32i3.1269

Authors

Sorapat NIYOMSIN The Petroleum and Petrochemical College, Chulalongkorn University, Bangkok 10330, Thailand; Center for Petroleum, Petrochemical, and Advance Materials, Chulalongkorn University, Bangkok 10330, Thailand
Suwabun CHIRACHANCHAI The Petroleum and Petrochemical College, Chulalongkorn University, Bangkok 10330, Center for Petroleum, Petrochemical, and Advance Materials, Chulalongkorn University, Bangkok 10330, ThailandThailand;
Toshikazu TAKATA Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan

DOI:

https://doi.org/10.55713/jmmm.v32i3.1269

Keywords:

Rotaxane, Benzoxazine, Light responsiveness, Supramolecule

Abstract

Rotaxanes are known for the mechanically interlocked molecules for decades. The present work demonstrates a method to prepare multi-responsive rotaxane by conjugating with a multi-responsive supramolecule. Benzoxazine dimers, N, N’-bis(3,5-dimethyl-2-hydroxybenzyl) methylamine derivatives, are good models because their simple chemistry. An azobenzene containing benzoxazine with remaining hydroxyl group for further conjugation with rotaxane was designed. The ring opening of rotaxane using fluorescent phenol provides benzoxazine dimer with metal ion responsive and fluorescent properties. Based on this concept, light responsive benzoxazine conjugated with rotaxane system shows light, metal ion and rotaxane shuttling responsiveness which can be followed by fluorescent signals. The present work shows simple way to develop rotaxanes with multi-responsive functions using supramolecular chemistry of benzoxazine dimer prepared from light responsive phenol.

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