Citation: Jia-Qi Zhang, Qiao-Chun Wang, Lei Zou, Chun-Yang Jia. Synthesis and properties of novel photochromic bisthienylethenes containing imidazole and imidazolium derivatives[J]. Chinese Chemical Letters, ;2014, 25(05): 762-766. doi: 10.1016/j.cclet.2014.01.033
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A series of bisthienylethenes containing imidazole and imidazolium derivatives have been prepared and the products have been characterized by means of NMR and MS. Their photochromic and fluorescent switch properties have been investigated by UV-vis absorption spectra and fluorescence spectra. The fluorescent emissions of these kinds of photochromic compounds can be simply modulated by varying the imidazole groups, which shows that these compounds may have potential application in the design of fluorescent photochromic materials.
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Keywords:
- Photochromism,
- Bisthienylethenes,
- Imidazole,
- Fluorescence
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[1]
[1] M. Irie, Diarylethenes for memories and switches, Chem. Rev. 100 (2000) 1685-1716.
-
[2]
[2] H. Tian, S.J. Yang, Recent progresses on diarylethene based photochromic switches, Chem. Soc. Rev. 33 (2004) 85-97.
-
[3]
[3] J.J. Zhang, Q. Zou, H. Tian, Photochromic materials: more than meets the eye, Adv. Mater. 25 (2013) 378-399.
-
[4]
[4] J.Q. Zhang, J.Y. Jin, L. Zou, H. Tian, Reversible photo-controllable gels based on bisthienylethene-doped lecithin micelles, Chem. Commun. 49 (2013) 9926-9928.
-
[5]
[5] C.R. Zhang, W.P. Yan, M.G. Fan, Synthesis and photoreaction mechanism of a novel bifunctional photochromic compound, Chin. Chem. Lett. 18 (2007) 519-522.
-
[6]
[6] Z.Y. Li, W. Xue, G.X. Liu, et al., Synthesis and properties of template-promoted switchabledithienylethene-basedmacrocycles, Chin.Chem. Lett. 24 (2013)189-191.
-
[7]
[7] G.Y. Jiang, S. Wang, W.F. Yuan, et al., Photo- and proton-dual-responsive fluorescence switch based on a bisthienylethene-bridged naphthalimide dimer and its application in security data storage, Eur. J. Org. Chem. 13 (2007) 2064-2067.
-
[8]
[8] S. Pu, C. Zheng, Q. Sun, G. Liu, C. Fan, Enhancement of cyclization quantum yields of perfluorodiarylethenes via weak intramolecular interactions, Chem. Commun. 49 (2013) 8036-8038.
-
[9]
[9] G. Liu, S.Z. Pu, R.J. Wang, Photochromism of asymmetrical diarylethenes with a pyrrole unit: effects of aromatic stabilization energies of aryl rings, Org. Lett. 15 (2013) 980-983.
-
[10]
[10] Q. Zou, X. Li, J. Zhang, et al., Unsymmetrical diarylethenes as molecular keypad locks with tunable photochromism and fluorescence via Cu2+ and CN- coordinations, Chem. Commun. 48 (2012) 2095-2097.
-
[11]
[11] J.Q. Zhang, J.Y. Jin, J.J. Zhang, L. Zou, An optic/proton dual-controlled fluorescence switch based on novel photochromic bithienylethene derivatives, Chin. J. Chem. 30 (2012) 1741-1747.
-
[12]
[12] U. Al-Atar, R. Fernandes, B. Johnsen, D. Baillie, N.R. Branda, A photocontrolled molecular switch regulates paralysis in a living organism, J. Am. Chem. Soc. 131 (2009) 15966-15967.
-
[13]
[13] S.Z. Pu, D.H. Jiang, W.J. Liu, G. Liu, S.Q. Cui, Multi-addressable molecular switches based on photochromic diarylethenes bearing a rhodamine unit, J. Mater. Chem. 22 (2012) 3517-3526.
-
[14]
[14] J.J. Zhang, W.J. Tan, X.L. Meng, H. Tian, Soft mimic gear-shift with a multi-stimulus modified diarylethene, J. Mater. Chem. 19 (2009) 5726-5729.
-
[15]
[15] S.Z. Pu, Z.P. Tong, G. Liu, R.J. Wang, Multi-addressable molecular switches based on a new diarylethene salicylal Schiff base derivative, J. Mater. Chem. C 1 (2013) 4726-4739.
-
[16]
[16] W.H. Zhu, Y.H. Yang, R. Métivier, et al., Unprecedented stability of a photochromic bisthienylethene based on benzobisthiadiazole as an ethene bridge, Angew. Chem. Int. Ed. 50 (2011) 10986-10990.
-
[17]
[17] X.L. Meng, W.H. Zhu, Q. Zhang, et al., Novel bisthienylethenes containing naphthalimide as the center ethene bridge: photochromism and solvatochromism for combined NOR and INHIBIT logic gates, J. Phys. Chem. B 112 (2008) 15636-15645.
-
[18]
[18] E. Oliveira, R.M. Baptista, S.P. Costa, M.M. Raposo, C. Lodeiro, Exploring the emissive properties of new azacrown compounds bearing aryl, furyl, or thienyl moieties: a special case of chelation enhancement of fluorescence upon interaction with Ca2+, Cu2+, or Ni2+, Inorg. Chem. 49 (2010) 10847- 10857.
-
[19]
[19] G.P. Duan, N.Y. Zhu, V.W. Yam, Syntheses and photochromic studies of dithienylethene- containing imidazolium derivatives and their reactivity towards nucleophiles, Chem. Eur. J. 16 (2010) 13199-13209.
-
[20]
[20] Z. Li, J. Xia, J. Liang, et al., Synthesis of diarylethene derivatives containing various heterocycles and tuning of light-emitting properties in a turn-on fluorescent diarylethene system, Dyes Pigments 90 (2011) 290-296.
-
[21]
[21] H.H. Liu, Y. Chen, Selective photoconversion of photochromic diarylethenes and their properties, New J. Chem. 36 (2012) 2223-2227.
-
[22]
[22] M.P. Vladimirova, S.D. Simova, E.R. Stanoeva, M.I. Mitewa, Synthesis and spectroscopic properties of new Schiff bases containing the N-phenylaza-15-crown-5 moiety, Dyes Pigments 50 (2001) 157-162.
-
[23]
[23] L. Belen'kii, V. Shirinyan, G. Gromova, et al., A new approach to the synthesis of dithienylethanediones and dithienylacetylenes, Chem. Heterocycl. Compd. 39 (2003) 1570-1579.
-
[24]
[24] S. Nakamura, M. Irie, Thermally irreversible photochromic systems. A theoretical study, J. Org. Chem. 53 (1988) 6136-6138.
-
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