Synthesis and Properties of Novel Dual-Color Fluorescent Molecular Switch with 1,8-Naphthalimide Unit

doi:10.6023/cjoc201708062

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (2): 425-431.DOI: 10.6023/cjoc201708062 Previous Articles Next Articles

Special Issue: 有机超分子化学合辑

Articles

新型1,8-萘酰亚胺类光控双色荧光分子开关的合成及性质

杨素华^a, 闫素君^b, 杨静^a, 张策^a, 韩国英^a

a 赤峰学院化学化工学院内蒙古自治区光电功能重点实验室赤峰 024000;
b 中山大学化学与化学工程学院广州 510275

收稿日期:2017-08-30 修回日期:2017-09-11 发布日期:2017-10-24
通讯作者: 杨素华 E-mail:cfyangsuhua@126.com
基金资助:
国家自然科学基金（No.21563002）、内蒙古自治区科学技术研究院（No.DBFY201301）和内蒙古自治区高等学校科学研究基金（No.NJZY241）资助项目.

Synthesis and Properties of Novel Dual-Color Fluorescent Molecular Switch with 1,8-Naphthalimide Unit

Yang Suhua^a, Yan Sujun^b, Yang Jing^a, Zhang Ce^a, Han Guoying^a

a Inner Mongolia Key Laboratory of Photoelectric Functional Materials, School of Chemistry and Chemical Engineering, Chifeng College, Chifeng 024000;
b School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275

Received:2017-08-30 Revised:2017-09-11 Published:2017-10-24
Contact: 10.6023/cjoc201708062 E-mail:cfyangsuhua@126.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21563002), the Inner Mongolia Science and Technology Institute Co., Ltd. (No. DBFY201301), and the Research Program of Science at Universities of Inner Mongolia Autonomous Region (No. NJZY241).

1. Synthesis and Properties of Novel Dual-Color Fluorescent Molecular Switch with 1,8-Naphthalimide Unit.PDF(509KB)

Abstract

Spiropyran compound is widely used as an important class of photochromic compounds. Three new types of 1, 8-naphthalimide compounds with spiropyran unit were synthesized and the structures were characterized. The photochromic characteristics research shows that their response time of the ring opening process is long even difficult to be detected comparing the classical spiropyran. And the reason of their prolonged ring opening reaction is analyzed theoretically and structurally. The photochromic properties of SP3 are more obvious both in solid medium and organic solvents due to the presence of the strong electro-withdraw substituent. It turned into orange red from yellow in polyethylene glycol (200) and from yellow to grey purple in acetone. The investigation of the UV-Vis absorption spectra also showed its negative solvent effect in different organic solvents. There is no significant difference in the absorption wavelength of the spiropyran unit ring opened after irradiation compared with the standard one. The fluorescence properties of the three compounds were investigated to find that SP1 and SP2 showed obvious fluorescence color changes prior and after the UV irradiation in the silica gel, and no fluorescence color changes were detected in polymethylmethacrylate (PMMA) and organic solvents. Fluorescence changes of compound SP3 in acetone were not detected after the UV irradiation. The compound SP3 emitted green fluorescence and became orange yellow fluorescence after ultrasonic irradiation in polyethylene glycol (200). The changing process was detected by fluorescence spectrum. The fluorescence color change of SP3 is more obvious in the thin layer silica gel before and after irradiation. As time elapses, the green fluorescence converted to red one and turned into red from orange yellow eventually. The fluorescence spectrum of the compounds in PMMA film showed that the compound SP3 played the role of a dual-color fluorescent molecular switch. Because of the amino-group in its molecular structure, this dual-color fluorescent molecular switch is suitable for application in labeling biological system.

Key words: photochromism, spiropyran, 1,8-naphthalimide, Dual-Color fluorescent molecular switch

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Yang Suhua, Yan Sujun, Yang Jing, Zhang Ce, Han Guoying. Synthesis and Properties of Novel Dual-Color Fluorescent Molecular Switch with 1,8-Naphthalimide Unit[J]. Chin. J. Org. Chem., 2018, 38(2): 425-431.

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新型1,8-萘酰亚胺类光控双色荧光分子开关的合成及性质

Synthesis and Properties of Novel Dual-Color Fluorescent Molecular Switch with 1,8-Naphthalimide Unit

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