Progress in Research of Bifunctional Spirobenzopyran and Spi-ronaphthooxazine Photochromic Compounds

Abstract

Photochromic materials have a wide range of applications such as ophthalmic lenses, optical information storages and optical molecular switches. More and more attention was paid to the synthesis and application of bifunctional photochromic materials. This article introduces the bifunctional photochromic materials based on spirobenzopyran and spirooxazine, in which special efforts have been given to the photochromic compounds which have fluorescent and metal coordination of photochromes.

Key words: photochromism, fluorescence, metal complex, polymer

Cite this article

YANG Su-Hua, PANG Mei-Li, MENG Ji-Ben. Progress in Research of Bifunctional Spirobenzopyran and Spi-ronaphthooxazine Photochromic Compounds[J]. Chin. J. Org. Chem., 2011, 31(11): 1725-1735.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

1 Irie, M. Chem.Rev. 2000, 100, 1683.

2 Zhang, P.; Meng, J.-B.; Matsuura, T.; Wang, Y.-M. Chinese Chemical Letters. 2002, 13, 299.

3 Fissi, A.; Pieroi, O.; Ruggeri, G.; Ciarde1li, F. Macromolecules, 1995, 28, 302.

4 Benniston, A. C.; Harriman ,A.; Howell, S. L.; Li, P.-Y.; Lydon, D. P. J. Org. Chem. 2007, 72, 888.

5 Roxburgh, C. J. ; Sammes P.G.. Eur. J. Org. Chem. 2006, 1050.

6 Taguchi, M.; Li ,G.-M.; Gu, Z.-Z.; Sato, O.; Einaga, Y. Chem. Mater. 2003, 15, 4756.

7 Such, G. K.; Evans, R.A.; Davis ,T. P. Macromolecules ,2006, 39, 9562.

8 Li, L.-L.; Liu, H.; Yang, Z.-H.; He, Y.; Ye, C.-P. Progress in Chemistry.2009, 21, 654

(李陵岚,刘　辉,杨泽慧,何　应,叶楚平,化学进展, 2009，21，654.)

9 Yildiz, I.; Deniz , E.; Raymo, F. M. Chem. Soc. Rev. 2009, 38, 1859.

10 Guo, X.-F.; Zhang, D.-Q.; Zhou,Y.-C.; Zhu, D.-B. J. Org. Chem. 2003, 68, 5681.

11 Guo, X.-F.; Zhang, D.-Q.; Zhou,Y.-C.; Zhu, D.-B. Adv. Mater. 2004, 16, 125.

12 Tomasulo, M.; Kaanumal, S. L.; Sortino, S.; Raymo, F. M. J. Org. Chem. 2007, 72, 595.

13 Meng, X.-L.; Zhu, W.-H.; Guo, Z.-Q,; Wang, J.-Q.; Tian, H. Tetrahedron , 2006 , 62 , 9840.

14 Yuan, W.-F.; Sun, L.; Tang, H.-H.; Wen,Y.-Q.; Jiang, G.-Y.; Huang, W.-H.; Jiang, L.; Song, Y.-L.; Tian, H.; Zhu, D.-B. Adv. Mater. 2005, 17, 156.

15 Wang, S.; Yu, C.-Y.; Choi, M.S.; Kim, S.H. J . Photochem. and Photobiol . A:Chem. 2007, 192, 17.

16 Chan W- L, Young Ho Song, Youngil Lee, Kwang Sun Ryu and Ki-Whan Chi* Chem. Commun., 2009, 6282–6284

17 Zhu, M.-Q.; Zhu,L.-Y.; Han, J. J.; Wu,W.-W.; Hurst, J. K.; Li , A.D. Q. J. Am. Chem. Soc. 2006, 128, 4303.

18 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.

19 Tian, Z.-Y.; Wu, W.-W.; Wan,W.; Li , A.D. Q. J. Am. Chem. Soc. 2009, 131, 4245.

20 Sunamoto, J.; Iwamoto, K.; Mohri,Y.; Kominato,T. J. Am. Chem. Soc. 1982, 104, 5502

21 Ipe, B. I.; Mahima, S.; Thomas, K. G.. J. Am. Chem. Soc. 2003, 125, 7174.

22 Shao, N.; Jin,J.-Y.; Wang,H. Zheng, J.; Yang, R.-H.; Chan,W.-H.; Abliz, Z. J. Am. Chem. Soc. 2010, 132, 725.

23 Feng, C.-G.; Wang, J.-Y. Chin. J. Org. Chem. 2006, 26, 1012(in Chinese).

(冯长根，王建营，有机化学，2006，26，1012.)

24 Kumar,S.; Watkins ,D.L.; Fujiwara ,T. Chem. Commun. 2009, 4369.

25 Guo, X.-F.; Zhou,Y.-C.; Zhang, D.-Q.; Yin, B.; Liu, Z.-L.; Liu, C.-M.; Lu, Z.-L.; Huang,Y.-H.; Zhu, D.-B. J. Org. Chem. 2004, 69, 8924.

26 Liu, Z.-L.; Jiang, L.; Liang, Z.; Gao,Y.-H. Tetrahedron Letters. 2005, 46, 885.

27 Shao, N.; Zhang,Y.; Cheung,S.-M. Yang,R.-H.; Chan,W.-H.; Mo,T.; Li, K.-A.; Liu, F.Anal. Chem. 2005, 77, 7294.

28 Zhu, J.-F.; Yuan,Han.; Chan,W.-H.; Lee, A. W. M. Tetrahedron Letters .2010.

29 Jeliazkova, B.G.; Minkovskab, S.; Deligeorgieva, T. J . Photochem. and Photobiol . A:Chem. 2005, 171, 153.

30 Kopelman, R. A.; Snyder,S. M.; Frank, N. L. J. Am. Chem. Soc. 2003, 125, 13684.

31 Paquette, M. M.; Kopelman, R. A.; Beitler, E.; Frank, N. L. Chem. Commun. 2009, 5424.

32 Yam,V. W.-W.; Ko,C.-C.; Wu, L.-X.; Wong, K. M.-C. ; Cheung ,K.-K. Organometallics. 2000, 19, 1820.

33 Ko, C.-C.; Wu, L.-X.; Wong, K. M.-C.; Zhu,N.-Y.; Yam, V. W.-W.Chem. Eur. J. 2004, 10, 766 .

34 Bao, Z.-H.; Ng, K.-Y.; Yam, V. W.-W.; Ko,C.-C.; Zhu, N.-Y.; Wu, L.-X. Inorganic Chemistry. 2008, 47, 8912.

35 Jukes, R. T. F.; Bozic, B.; Hartl, F.; Belser, P.; De Cola , L. Inorganic Chemistry. 2006, 45, 8326.

36 Jukes, R.T. F.; Bozic, B.; Belser, P.; De Cola , L.; Hartl, F. Inorganic Chemistry. 2009, 48, 1711.

37 Nagashima, S.; Murata, M.; Nishihara, H. Angew. Chem. 2006, 118, 4404 .

38 Alfimov,M. V.; Fedorova, O. A.; Gromov, S. P. J . Photochem. and Photobiol . A:Chem. 2003, 158, 183.

39 Kimura, K.; Nakahara, Y. Analytical Sciences. 2009, 25, 9.

40 Inouye, M.; Akamatsu, K.; Nakazumi, H. J. Am. Chem. Soc. 1997, 119, 9160.

41 Tsubaki,K.; Mukoyoshi ,K.; Morikawa, Hiroshi.; Kinoshita,T.; Fuji, K. Chirality. 2002, 14, 713.

42 Cheong , I. W.; Wang ,S.; Ki ,H. S.; Kim ,S.-H. Current Applied Physics. 2009, 9, 1269.

43 Shiraishi, Y.; Miyamoto, R.; Hirai T. Org. Lett. 2009, 11, 1571.

44 Davis, D. A.; Hamilton, A.; Yang, J.-L.; Cremar, L. D.; Gough, D. V.; Potisek, S. L.; Ong, M.T.; Braun1, P. V.; Mart?′nez1,T. J.; White, S. R.; Moore1, J. S.; Sottos, N. R. Nature .2009, 459, 68.

45 Li, X.; Han, J.; Pang, M.-L.; Meng, J.-B. Chin. J. Org. Chem. 2007, 27, 696(in Chinese).

(李旭，韩杰，庞美丽，孟继本，有机化学，2007，27 ，696.)

46 Wang, C.-M.; Pan, G.-L.; Zhao,L.-H.; Fan, P.; Meng,X.-J.; Ming,Y.-F.; Fan, M.-G. Chin. J. Org. Chem. 2001, 21, 954(in Chinese).

(王聪敏，潘桂兰，赵利华，樊平，孟宪娟，明阳福，樊美公，有机化学，2001，21，954.)

47 Yang, S.-J.; Tian,H. Journal of Chemical Industry and Engineering. 2003, 54, 497(in Chinese).

（杨松杰，田　禾，化工学报，2003，54， 497.）　　　　　　　　　　

48 Lokshin,V.; Samat, A.; Metelitsa, A. V. Russian Chemical Reviews. 2002, 71, 893.

[1]	Simin Wu, Jiaxin Tang, Yujia Zhou, Xuetao Xu, Haoxing Zhang, Shaohua Wang. α-Glucosidase Inhibition Research of Derivatives Based on 2β-Acetoxyferruginol Scaffold Excluding Acetic Acid Group [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 613-621.
[2]	Jiyu Liu, Shengyu Li, Kuan Chen, Yin Zhu, Yuan Zhang. Triphenylamine-Based Ordered Mesoporous Polymer as a Metal-Free Photocatalyst for Oxidation of Thiols to Disulfide [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 605-612.
[3]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[4]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[5]	Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166.
[6]	Xu Liao, Zeyu Wang, Wufei Tang, Jinqing Lin. Progress in Porous Organic Polymer for Chemical Fixation of Carnbon Dioxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2699-2710.
[7]	Lu Liu, Shuguang Zhang, Renwei Hu, Xiaoxiao Zhao, Jingnan Cui, Weitao Gong. Synthesis and Properties of Phenolic Resin Polymers Based on Pillar[5]arene [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2808-2814.
[8]	Liangru Yang, Mengli Guo, Jinwei Yuan, Jiamei Wangx, Yuting Xia, Yongmei Xiao, Pu Mao. Research Progress on Pincer N-Heterocyclic Carbene Metal Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2002-2025.
[9]	Yi Zhang, Cheng-Zhuo Du, Ji-Kun Li, Xiao-Ye Wang. Recent Advances in Multi-Resonance Thermally Activated Delayed Fluorescence Materials Based on B,N-Heteroarenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1645-1690.
[10]	Kaichun Liang, Keyan Bai, Lei Dai, Yuan Liu, Zecong Ye, Yanping Huo. Design, Synthesis and Electroluminescent Properties of Multiresonant Thermally Activated Delayed Fluorescence Materials Based on Tetrahydroquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1799-1807.
[11]	Shengjie Jiang, Yang Wang, Xin Xu. Rare-Earth Metal Complexes-Catalyzed Dehydropolymerization of Methylamine-Boranes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1786-1791.
[12]	Xiaodong Yang, Xiaokang Zheng, Hailiang Dong, Jing Sun, Hua Wang. Research Progress of Circularly Polarized Thermally Activated Delayed Fluorescence Materials and Devices [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1292-1309.
[13]	Rui Wang, Lang Gao, Cen Zhou, Xiao Zhang. Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1136-1145.
[14]	Lijuan Xiao, Yanping Zhang, Miao Hong. Research Progress of Lewis Acid and Base Pairs Applied in Materials Chemistry [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 949-960.
[15]	Xuqin Zhong, Zhen Liu. Conformational Screening of the Catalyst System Containing Transition Metal and Flexible Ligand [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 734-741.

双功能螺吡喃螺噁嗪类光致变色化合物研究进展