Synthesis and Fluorescence Properties of a Novel Dendrimer

doi:10.6023/cjoc1201141

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (10): 1958-1964.DOI: 10.6023/cjoc1201141 Previous Articles Next Articles

Notes

一种新型树枝分子的合成及其荧光性质

罗蔓利, 钱鹰

东南大学化学化工学院南京 211189

收稿日期:2012-01-14 修回日期:2012-05-23 发布日期:2012-06-21
通讯作者: 钱鹰 E-mail:yingqian@seu.edu.cn
基金资助:
国家自然科学基金(No. 61178057)资助项目.

Synthesis and Fluorescence Properties of a Novel Dendrimer

Luo Manli, Qian Ying

School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Received:2012-01-14 Revised:2012-05-23 Published:2012-06-21
Supported by:
Project supported by the National Natural Science Foundation of China (No. 61178057).

Through palladium-catalyzed Heck reaction, a novel fluorescent dentrimer 1,2,4,5-tetra{4-[N,N-bis(4-pyridyl- vinyl)phenylamino]styryl}benzene (TPABPy) was synthesized by aromatic eight iodine-substituted 1,2,4,5-tetra{4-[N,N-bis- (4-iodinephenylamino)styryl]}benzene (TPABI) and 4-vinylpyridine. The dentrimer was characterized through IR, ¹H NMR and HRMS techniques. The maxima emission wavelengths in THF, ethyl acetate, dichloromethane, DMF and DMSO were 490, 493, 510, 536 and 543 nm, respectively. Stoke’s shift was 4717 (THF), 4969 (ethyl acetate), 5330 (dichloromethane), 6281 (DMF), 6398 (DMSO) cm^-1. The fluorescence lifetime for TPABPy was 1.29 ns with fluorescence quantum yield of 0.87 in THF. The fluorescent behavior of TPABPy in different pH was studied , and the fluorescent intensity maximum was in pH 2.41. The electrochemical properties were explored by cyclic voltammetry, the HOMO and LUMO energy levels of dentrimer were -4.94 and -2.38 eV, respectively.

Key words: fluorescent dentrimer, Heck reaction, solvent effect, fluorescent lifetimes, frontier orbital

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Luo Manli, Qian Ying. Synthesis and Fluorescence Properties of a Novel Dendrimer[J]. Chin. J. Org. Chem., 2012, 32(10): 1958-1964.

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[1] Zhou, M.-Y.; Wang, X.-M.; Jiang, W.-L.; Wang, D.-Q. J. Funct. Mater. 2008, 39, 1421 (in Chinese).

(周懋怡, 王筱梅, 蒋宛莉, 王德强, 功能材料, 2008, 39, 1421.)

[2] Albrecht, K.; Yamamoto, K. J. Am. Chem. Soc. 2009, 131, 2244.

[3] Cavaye, H.; Shaw, P. E.; Smith, A. R. G.; Burn, P. L.; Gentle, I. R.; James, M.; Lo, S.-C.; Meredith, P. J. Phys. Chem. C 2011, 115, 18366.

[4] Li, Q.-Q.; Huang, J.; Zhong, A. S.; Zhong, C.; Peng, M.; Liu, J.; Pei, Z.-G.; Huang, Z.-L.; Qin, J.-G.; Li, Z. J. Phys. Chem. B 2011, 115, 4281.

[5] Jana, D.; Ghorai, B. K. Tetrahedron Lett. 2012, 53, 197.

[6] Li, H.-Y.; Zhang, X.-Q.; Chi, Z.-G.; Xu, B.-J.; Zhou, W.; Liu, S.-W.; Zhang, Y.; Xu, J.-R. Org. Lett. 2011, 4, 557.

[7] Jiang, Y.-H.; Wang, Y.-C.; Wang, B. Yang, J.-B.; He, N.-N.; Qian, S.-X.; Hua, J.-L. Chem. Asian J. 2011, 6, 157.

[8] Lin, T.-C.; Huang, Y.-J.; Huang, B.-R.; Lee. Y.-H. Tetrahedron Lett. 2011, 52, 6748.

[9] Hrobarik, P.; Hrobarikova, V.; Sigmundova, I.; Zahradník, P.; Fakis, M.; Polyzos, I.; Persephonis, P. J. Org. Chem 2011, 76, 8725.

[10] He, G.-S.; Tan, L.-S.; Zheng, Q.-D.; Paras, N. P. Chem. Rev. 2008, 108, 1296.

[11] Ogawa, K.; Kobuke, Y. Org. Biomol. Chem. 2009, 7, 2241.

[12] Droumaguet, C. L.; Mongin, O.; Werts, M. H. V.; Blanchard-Desce, M. Chem. Commun. 2005, 2802.

[13] Bhaskar, A.; Ramakrishna, G.; Lu, Z.-K.; Twieg, R.; Hales, J. M.; Hagan, D. J.; Stryland, E. V.; Goodson, T. J. Am. Chem. Soc. 2006, 128, 11842.

[14] Lin, T.-C.; Lin, W.-L.; Wang, C.-M.; Fu, C.-W. Eur. J. Org. Chem. 2011, 913.

[15] Yan, Z.-Q.; Xu, B.; Dong, Y.-J.; Tian, W.-J.; Li. A.-W. Dyes Pigm. 2011, 90, 270.

[16] Ren, Y.; Xin, Q.; Tao, X.-T.; Wang, L.; Yu, X.-Q.; Yang, J.-X.; Jiang, M.-H. Novel Chem. Phys. Lett. 2005, 414, 255.

[17] Koeckelberghs, G.; Vangheluwe, M.; Picard, I.; Groof, L. D.; Verbiest, T.; Persoons, A.; Samyn, C. Macromolecules 2004, 37, 8536.

[18] Wang, H.-Y.; Chen, G.; Xu, X.-P.; Chen, H.; Ji, S.-J. Dyes Pigm. 2011, 88, 359.

[19] Grabowski, Z. R.; Rotkiewicz, K. Chem. Rev. 2003, 103, 3899．

[20] Krebs, F. C.; Spanggaard, H. J. Org. Chem. 2002, 67, 7189..

[21] Srividya, N.; Ramamurthy, P.; Ramakrishnan, V. T. Spectrochim. Acta A 1997, 53, 1751.

[22] Xia, H.-J.; He, J.-Y.; Peng, P.; Zhou, Y.-H.; Li, Y.-W.; Tian, W.-J. Tetrahedron Lett. 2007, 48: 5878.

[23] Lartia, R.; Allain, C.; Bordeau, G.; Schmidt, F.; Fiorini- Debuisschert, C.; Charra, F.; Teulade-Fichou, M.-P. J. Org. Chem. 2008, 73, 1732.

[24] Wang, X.-M.; Jin, F.; Chen, Z.-G.; Liu, S.-Q.; Wang, X.-H.; Duan, X.-M.; Tao, X.-T.; Jiang, M.-H. J. Phys. Chem. C 2011, 115, 777.

[25] Promarak, V.; Ichikawa, M.; Meunmart, D.; Sudyoadsuk, T.; Saengsuwana, S.; Keawin, T. Tetrahedron Lett. 2006, 47, 8951.

[26] Li, X.-C.; Kim, Y.-S.; Kim, S.-H.; Jun, K.; Son, Y.-A. Fibers Polym. 2009, 6, 740.

[27] Li, K.-P.; Qu, J.-L.; Xu, B.; Zhou, Y.-H.; Liu, L.- J.; Peng. P.; Tian, W.-J. New J. Chem. 2009, 33, 2122.

一种新型树枝分子的合成及其荧光性质

Synthesis and Fluorescence Properties of a Novel Dendrimer

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