合成了一系列具有不同取代基团的二芳烯化合物,研究了取代基对其电化学开关性能的影响.结果表明:化合物上不同取代基影响其电化学开关性能,与闭环态中取代基苯基上的电子向中心环转移的结果有关;取代基的吸电子性与供电子性对起始氧化电位作用显著,除乙氧基外,氯、氟、甲基、甲氧基在开环和闭环态中对起始氧化电位有较大影响.
A series of photochromic dithienylcyclopentenes bearing different substituent at one terminal benzene ring have been synthesized and the substituent effect on their electrochemical properties was investigated in details. The results indicated that the efficiency of electrochemical switching is dependent on the nature of substituents, and the ring-closure isomers of these compounds undergo intramolecular electron transfer from the phenyl-substituted group to the central cyclopentene unit too. The substituent effect on the oxidation potential, such as chlorine, fluorine, methoxyl or methyl group, was very remarkable in both ring-open and ring-closure isomers, with the exception of that of ethoxyl group. However, the oxidation potential changes of diarylethenes with electron-withdrawing groups, e.g. fluorine atom, are clearly different from that of diarylethenes with electron-donating groups.
参考文献
| [1] | H Dürr;H Bouas-Laurent.Photochromism:Molecules and Systems[M].Elsevier:Amsterdam,The Netherlands,1990 |
| [2] | G H Brown.Photochromism[M].New York:Wiley-Interscience,1971 |
| [3] | M G Fan;L Yu;W Zhao;J C Crano,R J Guglielmetti.Organic photochromic and thermochromic compounds[M].New York:Plenum Press,1999:195. |
| [4] | M Irie;K Uchida .[J].Bulletin of the Chemical Society of Japan,1998,71:985-996. |
| [5] | S Z Pu et al.[J].Tetrahedron,2005,61:6623-6629. |
| [6] | M Takeshita;M Irie .[J].Journal of Organic Chemistry,1998,63:6643-6649. |
| [7] | M Irie .[J].Advances in Polymer Science,1993,110:49-65. |
| [8] | T Ikeda;T Sasaki et al.[J].Nature,1993,361:428-430. |
| [9] | Y Atassi;J A Delaire;K J Nakatani .[J].Journal of Physical Chemistry,1995,99:16320-16326. |
| [10] | S L Gilat;S H Kawai;J M Lehn .[J].Journal of the Chemical Society,Chemical Communications,1993,1439-1441 |
| [11] | S L Gilat;S H Kawai;J M Lehn .[J].Chemistry A European Journal,1995,1:275. |
| [12] | T Kawai;T Kunitake;M Irie .[J].Chemistry Letters,1999,905-906 |
| [13] | T Suzuki;J I Nishida;T Tsuji .[J].Angewandte Chemie International Edition in English,1997,36:1329-1331. |
| [14] | C Joachim;J K Gimzewski;A Aviram .[J].Nature,2000,408:541-548. |
| [15] | D Bonifazi et al.[J].Angewandte Chemie International Edition,2003,42:4966-4970. |
| [16] | M Kenji;M Irie .[J].Journal of the American Chemical Society,2000,122:7195-7201. |
| [17] | Y Moriyama et al.[J].Organic Letters,2005,15:3315-3318. |
| [18] | B Gorodetsky;HD Samachetty et al.[J].Angewandte Chemie International Edition,2004,43:2812-2815. |
| [19] | S Z Pu et al.[J].Tetrahedron Letters,2006,47:6473-6477. |
| [20] | S Z Pu;T S Yang;G Z Li;J K Xu,B Chen .[J].Tetrahedron Letters,2006,47:3167-3171. |
| [21] | J. Ern;A. T. Bens;H.-D. Martin;S. Mukamel;D. Schmid;S. Tretiak;E. Tsiper;C. Kryschi .Reaction dynamics of photochromic dithienylethene derivatives[J].Chemical Physics: A Journal Devoted to Experimental and Theoretical Research Involving Problems of Both a Chemical and Physical Nature,1999(s1-3):115-125. |
| [22] | S Z Pu et al.[J].Acta Crystallographica,2005,C61:o599-o601. |
| [23] | A Peters et al.[J].Organic Letters,2003,5:1183-1186. |
| [24] | S Z Pu et al.[J].Acta Crystallographica,2005,E61:o4246-o4249. |
| [25] | W R Browne;J J D de Jong et al.[J].Chemistry A European Journal,2005,11:6430-6441. |
| [26] | M Irie et al.[J].Journal of the American Chemical Society,2000,122:4871-4876. |
| [27] | W R Browne;J J D de Jong et al.[J].Chemistry A European Journal,2005,11:6414-6429. |
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