含硫甲基的芴-苯结构化合物的合成、结构和性能

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (7): 1375.

含硫甲基的芴-苯结构化合物的合成、结构和性能

张展, 张利锋, 薛芸蓉, 杨榆, 冀海英, 陆嘉星, 王欢, 高国华

华东师范大学化学系, 上海市绿色化学与化工过程绿色化重点实验室, 上海 200062

收稿日期:2009-10-06 出版日期:2010-07-10 发布日期:2010-07-10
通讯作者: 高国华, 男, 博士, 教授, 博士生导师, 主要从事有机催化和功能材料的研究. E-mail: ghgao@chem.ecnu.edu.cn
基金资助:
国家自然科学基金(批准号: 20873041)和上海市重点学科建设项目(批准号: B409)资助.

Synthesis, Characterization and Properties of Fluorenyl Phenyl, Based Conjugated Organic Materials

ZHANG Zhan, ZHANG Li-Feng, XUE Yun-Rong, YANG Yu, JI Hai-Ying, LU Jia-Xing, WANG Huan, GAO Guo-Hua*

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China

Received:2009-10-06 Online:2010-07-10 Published:2010-07-10
Contact: GAO Guo-Hua. E-mail: ghgao@chem.ecnu.edu.cn
Supported by:
国家自然科学基金(批准号: 20873041)和上海市重点学科建设项目(批准号: B409)资助.

摘要/Abstract

摘要：

通过双Suzuki偶联反应一步合成了2种含硫甲基的芴-苯结构化合物2,7-二(4-硫甲基苯基)-9,9-二己基-芴(a)和2,7-二(2,6-二甲基-4-硫甲基苯基)-9,9-二己基-芴(b). 紫外-可见和荧光光谱以及分子轨道理论计算表明, 位阻较小的化合物a具有更好的共轭性能, 其最大紫外-可见吸收波长达到351 nm, 比两端苯基含4个邻位取代基的化合物b红移了38 nm; 化合物a的最大荧光发射波长达到410 nm, 为典型的蓝光化合物, 比化合物b红移了43 nm. 化合物a和b都具有较高的荧光量子产率, 分别为59%和65%, 在光电材料方面具有潜在的应用前景.

关键词: Suzuki偶联反应; 芴; 吸收光谱; 荧光光谱

Abstract:

Fluorene and its derivatives are important conjugated organic materials for electronic devices. Their oligomers and polymers are the promising blue light-emitting materials with extremely high photoluminescence, quantum yields, and thermal and oxidative stability. The substitutes and stereo of the conjugated compounds play an important role on their electronic properties. In this paper, two kinds of fluorenyl-phenyl oligormers with thiomethyl group such as 2,7-bis-(4-methylsulfanyl-phenyl)-9,9-dihexyl- fluorene(a) and 2,7-bis-(2,6-dimethyl-4-methylsulfanyl-phenyl)-9,9-dihexyl-fluorene(b) were synthesized via the double Suzuki-Miyaura cross-coupling in the presence of palladium catalysts. The theory and property investigation show that compound a is more conjugated than compound b. The maximum absorption and fluorescence emission wavelength of compound a are at 351 and 410 nm, respectively. In the contrast, the corresponding absorption and emission of compound b are blue-shift of 38 and 43 nm, respectively. In addition, the synthesized fluorenyl-phenyl oligormers a and b have high fluorescence quantum yields of 59% and 65%, respectively. The superior properties of the fluorenyl-phenyl oligormers make these compounds be candidates of organic light-emitting materials.

Key words: Suzuki coupling reaction; Fluorene; Absorption spectrum; Fluorescence spectrum

TrendMD:

张展, 张利锋, 薛芸蓉, 杨榆, 冀海英, 陆嘉星, 王欢, 高国华. 含硫甲基的芴-苯结构化合物的合成、结构和性能. 高等学校化学学报, 2010, 31(7): 1375.

ZHANG Zhan, ZHANG Li-Feng, XUE Yun-Rong, YANG Yu, JI Hai-Ying, LU Jia-Xing, .... Synthesis, Characterization and Properties of Fluorenyl Phenyl, Based Conjugated Organic Materials. Chem. J. Chinese Universities, 2010, 31(7): 1375.

参考文献

[1]Lee S. H., Nakamura T., Tsutsui T.. Org. Lett.[J], 2001, 3: 2005—2007
[2]Marsitzky D., Vestberg R., Blainey P., Tang B. T., Hawker C. J., Carter K. R.. J. Am. Chem. Soc.[J], 2001, 123(29): 6965—6972
[3]HU Xiao-Dan(胡小丹), SU Li(苏立), LIAO Qi(廖琪), ZHEN Chang-Gua(甄常刮), CHUAI Yu-Tao(啜玉清), ZUO De-Qing(邹德青). Chem. J. Chinese Universities(高等学校化学学报)[J], 2005, 26(10): 1900—1904
[4]GrellM., BradleyD. D. C., Inbasekaran M., Woo E. P.. Adv. Mater.[J], 1997, 9: 198—802
[5]WU Jiang-Yong(吴江勇), HUO Er-Fu(霍二福), WU Zhi-Bing(吴志兵), LI Ying(李瑛), XIE Ming-Gui(谢明贵), JIANG Qing(蒋青). Chem. J. Chinese Universities(高等学校化学学报)[J], 2008, 29(2): 332—335
[6]Kreyenschmidt M., Klaerner G., Fuhrer T., Ashenhurst J., Karg S., Chen W. D., Lee V. Y., Scott J. C., Miller R. D.. Macromolecules[J], 1998, 31: 1099—1103
[7]Scharf J., Strehblow H. H., Zeysing B., Terfort A.. J. Solid State Electrochem.[J], 2001, 5: 396—401
[8]Maiti S. K.. Chem. Phys.[J], 2007, 331: 254—260
[9]Reddy P., Jang S., Segalman R. A., Majumdar A.. Science[J], 2007, 315: 1568—1571
[10]Briseno A. L., Aizenberg J., Han Y. J., Penkala R. A., Moon H., Lovinger A. J., Kloc C., Bao Z.. J. Am. Chem. Soc.[J], 2005, 127: 12164—12165
[11]Shaporenko A., Brunnbauer M., Terfort A., Grunze M., Zharnikov M.. J. Phys. Chem. B[J], 2004, 108: 14462—14469
[12]Cuevasa J. C., Heuricha J., Paulya F., Wenzel W., Schn G.. Phase Transit.[J], 2004, 77: 175—189
[13]Perepichka I. I., Perepichka I. F., Bryce M. R., Plsson L. O.. Chem. Commum.[J], 2005: 3397—3399
[14]Schoevaars A. M., Kruizinga W. Zulstra R. W. J.. J. Org. Chem.[J], 1997, 62: 4943—4948
[15]Leeuw D. M., Simenon M. M. J., Brown A. R., Einerhand R. E. F.. Synth. Met.[J], 1997, 87: 53—59
[16]Frisch M. J., Trucks G. W., Schlegel H. B., et al.. Gaussian 03[CP], Pittsburgh PA: Gaussian, Inc., 2003