Synthesis and Photochromic Property of 1-(Spirobi[fluorene]- 2-yl)-3,4-bis(2,5-dimethylfuran-3-yl)-2,5-dihydro-1H-pyrrole

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (05): 659-664. Previous Articles Next Articles

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1-(2-螺二芴)-3,4-二[3-(2,5-二甲基呋喃)]-2,5-二氢吡咯的合成及光致变色性质的研究

李财花，郑春梅，曾和平*

(华南理工大学化学与化工学院功能分子研究所广州 510641)

收稿日期:2010-07-13 修回日期:2010-09-20 发布日期:2010-12-10
通讯作者: 曾和平 E-mail:zenghp@scnu.edu.cn

Synthesis and Photochromic Property of 1-(Spirobi[fluorene]- 2-yl)-3,4-bis(2,5-dimethylfuran-3-yl)-2,5-dihydro-1H-pyrrole

LI Cai-Hua, ZHENG Chun-Mei, ZENG He-Ping

(Institute of Functional Molecules, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China)

Received:2010-07-13 Revised:2010-09-20 Published:2010-12-10

A new photochromic spirobifluorene-diarylethenes with furan as heterocyclic aryl groups (7a), was designed and synthesized. Its structure was confirmed by FT-IR, NMR, MS techniques and elemental analy-sis. Its photochromism in hexane and acetonitrile was investigated. The results indicated that 7a showed good photochromic behavior, and the photochromic reaction rate and conversion in hexane were both higher than that in acetonitrile. The fluorescence emission in different solution was also tested and it was found that fluorescence intensity decreased along with the photochromism from open ring form to closed ring form under irradiation and there was large fluorescence emission blue-shift of 7a in polar solvent. Furthermore, the thermal stabilities of 7a and 7b were greatly improved owing to spirobifluorene and furan groups in the molecules. The thermal weight loss starting temperature of 7a was 100 ℃ higher than that of 8a.

Key words: spirobifluorene, diarylethene, fluorescence, photochromism, thermal stability

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LI Cai-Hua, ZHENG Chun-Mei, ZENG He-Ping. Synthesis and Photochromic Property of 1-(Spirobi[fluorene]- 2-yl)-3,4-bis(2,5-dimethylfuran-3-yl)-2,5-dihydro-1H-pyrrole[J]. Chin. J. Org. Chem., 2011, 31(05): 659-664.

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1-(2-螺二芴)-3,4-二[3-(2,5-二甲基呋喃)]-2,5-二氢吡咯的合成及光致变色性质的研究

Synthesis and Photochromic Property of 1-(Spirobi[fluorene]- 2-yl)-3,4-bis(2,5-dimethylfuran-3-yl)-2,5-dihydro-1H-pyrrole

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