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Microwave-assisted synthesis of novel spirooxazines and their photochromic behaviors in polymer matrices

XIAOLI YANG1,2, BAOJIE YANG1, YUANYUAN LIU1, HONGJUN ZHU1,*

Affiliation

  1. Department of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009 P. R. China
  2. School of Material Engineering, Jinling Institute of Technology, Nanjing 211169, P. R. China

Abstract

A series of 1,3,3 trimethylspiro[2H] indol 2,3 ′′--[ naphtho[2,1 b][1,4]oxazine derivatives (spirooxazine) w ere synthesized using the microwave method. Their photochromic behaviors in styrene butadiene styrene copolymer (SBS), polycarbonate (PC), and polymethylmethacrylate (PMMA) were investigated. Re sults show t hat the colored form of spirooxazine is more stable in polar PMMA and cause a blue shift in the absorption spectrum of merocyanine. Furthermore, a broad thermal relaxation time range was obtained, from 129 s to 1724s in PMMA, at 20 °C) through a structur al modification of 6 heterocycle and 9 acyloxy. These results present a new strategy for designing photochromic molecules that feature different and acceptable relaxation times..

Keywords

Spirooxazine, Photochromism, Polymer matrices, Thermal decoloration Fatigue resistance.

Citation

XIAOLI YANG, BAOJIE YANG, YUANYUAN LIU, HONGJUN ZHU, Microwave-assisted synthesis of novel spirooxazines and their photochromic behaviors in polymer matrices, Optoelectronics and Advanced Materials - Rapid Communications, 6, 11-12, November-December 2012, pp.1146-1152 (2012).

Submitted at: June 11, 2012

Accepted at: Oct. 30, 2012