Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(2): 425-431. doi: 10.6023/cjoc201708062 shu

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

Corresponding author: Yang Suhua, cfyangsuhua@126.com
Received Date: 30 August 2017
Revised Date: 11 September 2017
Available Online: 24 February 2017
Fund Project: 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)the Research Program of Science at Universities of Inner Mongolia Autonomous Region NJZY241the National Natural Science Foundation of China 21563002the Inner Mongolia Science and Technology Institute Co., Ltd. DBFY201301

Figures(8)

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.
- photochromism,
- spiropyran,
- 1, 8-naphthalimide,
- Dual-Color fluorescent molecular switch
1. [1]
  Fu, N. -N.; Wang, H.; Zhang, H. -S. J. Anal. Sci. 2008, 24, 233(in Chinese).
2. [2]
  Dong, X.; Zhang, J.; Wang, K. -M.; Fang, S.; Liu, Y.; Meng, S. -X.; Feng, Y. -Q. J. Ind. Eng. 2017, 34, 27(in Chinese).
3. [3]
  El-Betany, A. M. M.; McKeown, N. B. Tetrahedron Lett. 2012, 53, 808. doi: 10.1016/j.tetlet.2011.12.009
4. [4]
  Li, C. -Y.; Xu, F.; Li, Y. -F.; Zhou, K.; Zhou, Y. Anal. Chim. Acta 2012, 717, 122. doi: 10.1016/j.aca.2011.12.018
5. [5]
  Zhao, F. -F.; Wu, H. -W.; Liu, C. -X.; Mao, H. -F. Chin. J. Org. Chem. 2016, 36, 2689(in Chinese).
6. [6]
  Shen, B. -X.; Qian, Y. Chin. J. Org. Chem. 2016, 36, 774(in Chinese).
7. [7]
  Tomasulo, M.; Kaanumal, S. L.; Sortino, S.; Raymo, F. M. J. Org. Chem. 2007, 72, 595. doi: 10.1021/jo062004d
8. [8]
  Shiraishi, Y.; Miyamoto, R.; Hirai, T. Org. Lett. 2009, 11, 1571. doi: 10.1021/ol900188m
9. [9]
  Xie, X. -J.; Mistlberger, G.; Bakker, E. J. Am. Chem. Soc. 2012, 134, 16929. doi: 10.1021/ja307037z
10. [10]
  Champagne, B.; Plaquet, A.; Pozzo, J. -L.; Rodriguez, V.; Castet, F. J. Am. Chem. Soc. 2012, 134, 8101. doi: 10.1021/ja302395f
11. [11]
  Julià-López, A.; Hernando, J.; Ruiz-Molina, D.; Gonzalez-Monje, P.; Sedó, J.; Roscini, C. Angew. Chem., Int. Ed. 2016, 55, 15044. doi: 10.1002/anie.201608408
12. [12]
  Shiraishi, Y.; Shirakawa, E.; Tanaka, K.; Sakamoto, H.; Ichikawa, S.; Hirai, T. ACS Appl. Mater. Interfaces 2014, 6, 7554. doi: 10.1021/am5009002
13. [13]
  Zhang, G. -F.; Chen, T.; Li, C.; Gong, W. -L.; Aldred, M. P.; Zhu, M. -Q. Chin. J. Org. Chem. 2013, 33, 927(in Chinese).
14. [14]
  Chen, P.; Wang, Y. -Y.; Zhang, Y. -M.; Zhang, X. -A. Acta Chim. Sinica 2016, 74, 669(in Chinese). doi: 10.11862/CJIC.2016.069
15. [15]
  Chen, J. -Y.; Su, W.; Wang, E. -J. Chem. J. Chin. Univ. 2016, 37, 232(in Chinese). doi: 10.7503/cjcu20150563
16. [16]
  Zhu, L. -Y.; Wu, W. -W.; Zhu, M. -Q.; Han, J. J.; Hurst, J. K.; Li, A. D. Q. J. Am. Chem. Soc. 2007, 129, 3524. doi: 10.1021/ja068452k
17. [17]
  Tian, Z. -Y.; Wu, W. -W.; Wan, W.; Li, A. D. Q. J. Am. Chem. Soc. 2009, 131, 4245. doi: 10.1021/ja805150g
18. [18]
  Bereau, V.; Jubera, V.; Arnaud, P.; Kaiba, A.; Guionneau, P.; Sutter, J. P. Dalton Trans. 2010, 39, 2070. doi: 10.1039/b918235g
19. [19]
  Liu, X.; He, W. Chem. Reag. 2001, 23, 237(in Chinese). doi: 10.3969/j.issn.0258-3283.2001.04.017
20. [20]
  Keum, S. -R.; Lee, J. -H.; Seok, M. -K. Dyes Pigm. 1994, 25, 21. doi: 10.1016/0143-7208(94)80015-4
21. [21]
  Warshawsky, A.; Kahana, N.; Buchholtz, F.; Zelichonok, A.; Krongauz, V. Ind. Eng. Chem. Res. 1995, 34, 2825. doi: 10.1021/ie00047a036
1. [1]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
2. [2]
  Zishuo Yi , Peng Liu , Yan Xu . Fluorescent “Chameleon”: A Popular Science Experiment Based on Dynamic Luminescence. University Chemistry, 2024, 39(9): 304-310. doi: 10.12461/PKU.DXHX202311079
3. [3]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
4. [4]
  Huirong LIU , Hao XU , Dunru ZHU , Junyong ZHANG , Chunhua GONG , Jingli XIE . Syntheses, structures, photochromic and photocatalytic properties of two viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1368-1376. doi: 10.11862/CJIC.20240066
5. [5]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
6. [6]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
7. [7]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
8. [8]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
9. [9]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
10. [10]
  Lianghong Ye , Junqing Ni , Zhongyi Yan , Zhanming Zhang , Can Zhu , Mo Sun . Chemical Fuel-Driven Non-Equilibrium Color Change. University Chemistry, 2025, 40(3): 349-354. doi: 10.12461/PKU.DXHX202406109
11. [11]
  Jiatong Hu , Qiyi Wang , Ruiwen Tang , Jiajing Feng . Photocatalytic Journey of Perylene Diimides in a Competitive Arena. University Chemistry, 2025, 40(5): 328-333. doi: 10.12461/PKU.DXHX202407015
12. [12]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
13. [13]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
14. [14]
  Ji Qi , Jianan Zhu , Yanxu Zhang , Jiahao Yang , Chunting Zhang . Visible Color Change of Copper (II) Complexes in Reversible SCSC Transformation: The Effect of Structure on Color. University Chemistry, 2024, 39(3): 43-57. doi: 10.3866/PKU.DXHX202307050
15. [15]
  Tongyu Zheng , Teng Li , Xiaoyu Han , Yupei Chai , Kexin Zhao , Quan Liu , Xiaohui Ji . A DIY pH Detection Agent Using Persimmon Extract for Acid-Base Discoloration Popularization Experiment. University Chemistry, 2024, 39(5): 27-36. doi: 10.3866/PKU.DXHX202309107
16. [16]
  Yi Li , Zhaoxiang Cao , Peng Liu , Xia Wu , Dongju Zhang . Revealing the Coloration and Color Change Mechanisms of the Eriochrome Black T Indicator through Computational Chemistry and UV-Visible Absorption Spectroscopy. University Chemistry, 2025, 40(3): 132-139. doi: 10.12461/PKU.DXHX202405154
17. [17]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
18. [18]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
19. [19]
  Feng Zheng , Ruxun Yuan , Xiaogang Wang . “Research-Oriented” Comprehensive Experimental Design in Polymer Chemistry: the Case of Polyimide Aerogels. University Chemistry, 2024, 39(10): 210-218. doi: 10.12461/PKU.DXHX202404027
20. [20]
  Jianding LI , Junyang FENG , Huimin REN , Gang LI . Proton conductive properties of a Hf(Ⅳ)-based metal-organic framework built by 2,5-dibromophenyl-4,6-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1094-1100. doi: 10.11862/CJIC.20240464

Get Citation

PDF

XML

Metrics

PDF Downloads(17)
Abstract views(2338)
HTML views(521)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142