Synthesis, Properties and Application in Optical Memory of a Photochromic Diarylethene Bearing Pyrimidine and Pyridine Ring

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Abstract:

A new photochromic diarylethene compound, 1-(2,4-dimethoxy-5-pyrimidine)-2-[2-methyl-5-(3-pyridine)-3-thienyl]perfluorocyclopentene(1a), was synthesized, and its photochromic reactivity, fluorescent and electrochemical property were also investigated. Diarylethene 1a changed the color from colorless to pink upon irradiation with UV light, in which absorption maxima were observed at 520 and 519 nm in hexane and PMMA film, respectively. The the photochromic reaction kinetics indicated that the cyclization processes of 1 belong to the zeroth order reaction and the cycloreversion process belong to the first order reaction. This new photochromic system also exhibited remarkable fluorescence switching in hexane solution and this new photochromic system also exhibited remarkable optical storage character.

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Advanced Materials Research (Volumes 490-495)

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3733-3737

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March 2012

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© 2012 Trans Tech Publications Ltd. All Rights Reserved

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[1] G.H. Brown, Photochromism; Molecules and System, New York, Wiley-Interscience, (1971).

Google Scholar

[2] T. Kawai, Y. Nakashima, M. Irie, A Novel Photoresponsive π-Conjugated Polymer Based on Diarylethene and its Photoswitching Effect in Electrical Conductivity, Adv. Mater. 17 (2005) 309-314.

DOI: 10.1002/adma.200400191

Google Scholar

[3] J.M. Andrew, G. Brain, N.R. Branda, Photoregulation of Luminescence Quenching in Photochromic Porphyrin–Phenoxynaphthacene- quinone Copolymers, Adv. Mater. 16 (2004) 922-925.

DOI: 10.1002/adma.200306227

Google Scholar

[4] S.H. Chen, H.M.P. Chen, Y. Geng, S.D. Jacobs, K.L. Marshall, T.N. Blanton, Novel Glassy Nematic Liquid Crystals for Non-destructive Rewritable Optical Memory and Photonic Switching, Adv. Mater. 15 (2003) 1061-1065.

DOI: 10.1002/adma.200304836

Google Scholar

[5] K. Uchida, A. Takata, M. Saito, A. Murakami, S. Nakamura, M. Irie, A Novel Photochromic Film by Oxidation Polymerization of a Bisbenzothienylethene with Phenol Groups, Adv. Mater. 15 (2003) 785-788.

DOI: 10.1002/adma.200304562

Google Scholar

[6] H. Tian, B. Chen, H.Y. Tu, K. Mu¨llen, Novel Bisthienylethene-Based Photochromic Tetraazaporphyrin with Photoregulating Luminescence, Adv. Mater. 14 (2002) 918-923.

DOI: 10.1002/1521-4095(20020618)14:12<918::aid-adma918>3.0.co;2-y

Google Scholar

[7] F.M. Raymo, M. Tomasulo, Electron and energy transfer modulation with photochromic switches, Chem. Soc. Rev. 34 (2005) 327-336.

DOI: 10.1039/b400387j

Google Scholar

[8] M. Irie, Diarylethenes for Memories and Switches, Chem. Rev. 100 (2000) 1685-1716.

DOI: 10.1021/cr980069d

Google Scholar

[9] Y. Chen, D.X. Zeng, N. Xie, Y.Z. Dang, Study on photochromism of diarylethenes with a 2, 5-dihydropyrrole bridging unit: a convenient preparation of 3, 4-diarylpyrroles from 3, 4-diaryl-2, 5-dihydropyrroles, J. Org. Chem. 70 (2005) 5001-5005.

DOI: 10.1021/jo050236r

Google Scholar

[10] T. Fukaminato, T. Sasaki, T. Kawai, N. Tamai , M. Irie, Digital photo-switching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level, J. Am. Chem. Soc. 126 (2004) 14843-14849.

DOI: 10.1021/ja047169n

Google Scholar

[11] S.Z. Pu, F.S. Zhang, J.K. Xu, L. Shen, Q. Xiao, B. Chen, Photochromic diarylethene for three-wavelength optical memory, Mater. Lett. 60 (2006) 485-489.

DOI: 10.1016/j.matlet.2005.09.021

Google Scholar

[12] H. Tian, S.J. Yang, Recent progresses on diarylethene based photochromic switches, Chem. Soc. Rev. 33 (2004) 85-97.

DOI: 10.1039/b302356g

Google Scholar

[13] K. Higashiguchi, K. Matsuda, N. Tanifuji, M. Irie, Full-color photochromism of a fused dithienylethene trimer, J. Am. Chem. Soc. 127 (2005) 8922-8923.

DOI: 10.1021/ja051467i

Google Scholar

[14] K. Matsuda, M. Irie, Diarylethene as a photoswitching unit, J. Photochem. Photobiol. C: Photoch. Rev. 5 (2004) 169-182.

Google Scholar

[15] M. Morimoto, M. Irie, Photochromism of diarylethene single crystals: crystal structures and photochromic performance, Chem. Commun. 2005 3895-3905.

DOI: 10.1039/b505256d

Google Scholar

[16] S.Z. Pu, T.S. Yang, J.K. Xu, L. Shen, G.Z. Li, Q. Xiao, B. Chen, Syntheses and optoelectronic properties of four photochromic dithienylethenes, Tetrahedron. 61 (2005) 6623-6629.

DOI: 10.1016/j.tet.2005.04.044

Google Scholar

[17] M. Irie, Photoswitchable Molecular Systems Based on Diarylethenes, Weinheim, Wiley-VCH, (2001).

Google Scholar

[18] K. Kasatani, S. Kambe, M. Irie, Photochromic reaction and fuorescence of dithienylethenes in the solid state, J. Photochem. Photobiol. A. 122 (1999) 11-15.

DOI: 10.1016/s1010-6030(99)00016-7

Google Scholar

[19] C.B. Fan, S.Z. Pu, G. Liu, T.S. Yang, Substituent position effect on the properties of isomeric photochromic diarylethenes bearing chlorine atoms, J. Photoch. Photobiol. A. 194 (2008) 333-343.

DOI: 10.1016/j.jphotochem.2007.08.032

Google Scholar