Preparation and Characterization of Phenanthroimidazole-based Derivatives with Ether Linkage at N1-Phenyl†

doi:10.7503/cjcu20140044

Abstract

Abstract:

1,2-Diphenyl-1H-phenanthro[9,10-d]imidazole(PPI), as a model compound for PI-based compound in optoelectronic researches, exhibits good deep-blue emission with high color purity in solid, but has too bad thermal ability to apply as an emitter because its film would break under annealing. Based on the structure-property relationship of PI block, the newborn structure ONBPPI was prepared and confirmed by NMR spectra. It had the same substituted group at C2-position to PPI, and was introduced the ether linkage at N1-phenyl which was different to PPI at N1-position. The analysis of TGA and DSC showed that the thermal ability was enhanced accompany with the molecular weight increase from PPI to ONBPPI. AFM graphs showed that the film of ONBPPI had better stability than PPI in annealing at 90 ℃ for 2 h. And the similar fluorescence spectra in single molecular with fine split delivered that the unchanged transition process existed in both. In the film, a little blue-shift was observed in ONBPPI, which implied that the aggregation effect was weakened because of the ether bond insert. The phenomenon of the proportion of low-energy level emission increase in solid fluorescence spectra was found, but there was no obvious effect on deep-blue color. All of these results were consisted with our expected, and this strategy of enhancing multi-functions on PPI was realized under unchanged transition process by inserting ether linkage at N1-phenyl.

Key words: Phenanthroimidazole, Ether bond, Thermal property, Fluorescence spectrum, Color purity

TrendMD:

WANG Zhiming, FENG Ying, LI Hui, SONG Xiaohui, LU Ping. Preparation and Characterization of Phenanthroimidazole-based Derivatives with Ether Linkage at N1-Phenyl^†[J]. Chem. J. Chinese Universities, 2014, 35(8): 1691.

Figures/Tables 3

References 21

[1]	Chaskar A., Chen H. F., Wong K. T., Adv. Mater., 2011, 23, 3876—3895
[2]	Zhu M. R., Yang C. L., Chem. Soc. Rev., 2013, 42, 4963—4976
[3]	Zhang Z., Wang Q., Wu Q., Hu X. Y., Wang C. X., Mei W. J., Tao Y. Y., Wu W. L., Zheng W. J., Chem. J. Chinese Universities, 2012, 33(11), 2441—2446
	(张召, 王淇, 吴琼, 胡晓莹, 王成蹊, 梅文杰, 陶韵伊, 吴韦黎, 郑文杰. 高等学校化学学报, 2012, 33(11), 2441—2446)
[4]	Zhou Y., Wang D. M., Zhao X. G., Zhou H. W., Chen C. H., Dang G. D., Chem. J. Chinese Universities, 2013, 34(10), 2427—2430
	(周宇, 王大明, 赵晓刚, 周宏伟, 陈春海, 党国栋. 高等学校化学学报, 2013, 34(10), 2427—2430)
[5]	Wang Z. M., Lu P., Chen S. M., Gao Z., Shen F. Z., Zhang W. S., Xu Y. X., Kwok H. S., Ma Y. G., J. Mater. Chem., 2011, 21, 5451—5456
[6]	Wang Z. M., Gao Z., Xue S. F., Liu Y. L., Zhang W. S., Gu C., Shen F. Z., Lu P., Ma Y. G., Polym. Bull., 2012, 69, 273—289
[7]	Wang Z. M., Song X. H., Gao Z., Yu D. W., Zhang X. J., Lu P., Shen F. Z., Ma Y. G., RSC Adv., 2012, 2, 9635—9642
[8]	Wang Z. M., Song X. H., Li H., Feng Y., Lu P., Chem. J. Chinese Universities, 2014, 35(3), 505—510
	(王志明, 宋晓慧, 李辉, 冯颖, 路萍. 高等学校化学学报, 2014, 35(3), 505—510)
[9]	Chen S. M., Zhao Z. J., Wang Z. M., Lu P., Gao Z., Ma Y. G., Tang B. Z., Kwok H. S., J. Phys. D. Appl. Phys., 2011, 44, 145101-1—145101-9
[10]	Gao Z., Liu Y. L., Wang Z. M., Shen F. Z., Liu H., Sun G. N., Lv Y., Lu P., Ma Y. G., Chem. Eur. J., 2013, 19, 2602—2605
[11]	Zhang S. T., Li W. J., Yao L., Pan Y. Y., Shen F. Z., Xiao R., Yang B., Ma Y. G., Chem. Commun., 2013, 49, 11302—11304
[12]	Li W. J., Liu D., Shen F. Z., Ma D. G., Wang Z. M., Feng T., Xu Y. X., Yang B., Ma Y. G., Adv. Funct. Mater., 2012, 22, 2797—2803
[13]	Kuo C. J., Li T. Y., Lien C. C., Liu C. H., Wu F. I., Huang M. J., J. Mater. Chem., 2009, 19, 1865—1871
[14]	Zhang Y., Lai S. L., Tong Q. X., Lo M. F., Ng T. W., Chan M. Y., Wen Z. C., He J., Jeff K. S., Tang X. L., Liu W. M., Ko C. C., Wang P. F., Lee C. S., Chem. Mater., 2012, 24, 61—70
[15]	Zhang Y., Lai S. L., Tong Q. X., Chan M. Y., Ng T. W., Wen Z. C., Zhang G. Q., Lee S. T., Kwong H. L., Lee C. S., J. Mater. Chem., 2011, 21, 8206—8214
[16]	Huang H., Wang Y. X., Zhuang S. Q., Yang X., Wang L., Yang C. L., J. Phys. Chem. C, 2012, 116, 19458—19466
[17]	Zhuang S. Q., Shang R. G., Jin J. J., Tu G. L., Wang L., Chen J. S., Ma D. G., Zhu X. J., Org. Electro., 2012, 13, 3050—3059
[18]	Wang J. L., Lin W. Y., Li W. L., Biomaterials, 2013, 34, 7429—7437
[19]	Zhang X. Y., Lin J., Ouyang X. H., Liu Y., Liu X. Y., Ge Z. Y., J. Photochem. Photobiol. A, 2013, 268, 37—48
[20]	Yuan Y., Li D., Zhang X. Q., Zhao X. J., Liu Y., Zhang J. Y. Wang Y., New J. Chem., 2011, 35, 1534—1540
[21]	Yang F. F., Guo H. Y. , Xie J. W., Liu Z. Q., Xu B. T., Chem. Res. Chinese Universities, 2012, 28(2), 358—360