Investigation of Excited-State Proton Transfer of 2-(3-Acetamido-2-pyridyl)benzimidazole in the Confined Nanocavity of Cucurbit[7]uril

doi:10.6023/cjoc201212044

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1451-1456.DOI: 10.6023/cjoc201212044 Previous Articles Next Articles

Articles

七元瓜环纳米腔限制环境下2-(3-乙酰胺基-2-吡啶基)苯并咪唑的激发态质子转移

易平贵, 阳习春, 刘金, 侯博, 于贤勇, 李筱芳, 汪朝旭, 郑柏树

湖南科技大学化学化工学院湘潭 411201

收稿日期:2012-12-25 修回日期:2013-03-02 发布日期:2013-03-15
通讯作者: 易平贵 E-mail:pgyi@hnust.cn
基金资助:
国家自然科学基金(Nos. 21172066, 20971041);湖南省自然科学基金(Nos. 10JJ4011, 11JJ2007)和湖南省高校科技创新团队支持计划(No,[2012]318-17))资助项目.

Investigation of Excited-State Proton Transfer of 2-(3-Acetamido-2-pyridyl)benzimidazole in the Confined Nanocavity of Cucurbit[7]uril

Yi Pinggui, Yang Xichun, Liu Jin, Hou Bo, Yu Xianyong, Li Xiaofang, Wang Zhaoxu, Zheng Baishu

School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201

Received:2012-12-25 Revised:2013-03-02 Published:2013-03-15
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172066, 20971041), the Hunan Provincial Natural Science Foundation of China (No. 11JJ2007), the Science and Technology Innovative Research Team in Higher Educational Instituions of Hunan Province (No.[2012]318-17).

The interaction of 2-(3-acetamido-2-pyridyl)-benzimidazole (2-3Am2PyBI) with cucurbit[7]uril (CB7) macrocycle and the effect of inclusion on the proton transfer of 2-3Am2PyBI were studied by using emission fluorescence, 1H NMR spectra and quantum chemical calculation. By the way, the proton transfer of the dye with and without acetyl (2-3A2PyBI) was also studied. The results indicate that the acetyl promoted the process of proton transfer of the benzimidazole and the cationic form binds with CB7 easier than the other forms of the dye. The fluorescence studying at selected pHs suggest that the proton transfer process of the dye was retarded by interacting with CB7 nanocavity and the molar rate is host:guest=1:1 analyzed by the Benesi-Hildebrand method. The dye entered into the CB7 cavity with its benzene ring was proved by the ¹H NMR titration experiment and the protonated forms were verified by the quantum calculation with fluorescence spectra.

Key words: proton transfer, cucurbit[7]uril, emission fluorescence, ¹H NMR spectra, quantum calculation

Cite this article

Yi Pinggui, Yang Xichun, Liu Jin, Hou Bo, Yu Xianyong, Li Xiaofang, Wang Zhaoxu, Zheng Baishu. Investigation of Excited-State Proton Transfer of 2-(3-Acetamido-2-pyridyl)benzimidazole in the Confined Nanocavity of Cucurbit[7]uril[J]. Chin. J. Org. Chem., 2013, 33(07): 1451-1456.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Weller, A. Z. Elektrochemie 1956, 60, 1144. (b) Luque, A. M.; Mulder, W. H.; Calvente, J. J.; Cuesta, A.; Andreu, R. Anal. Chem. 2012, 84, 5778. (c) Presiado, I.; Gepshtein, R.; Erez, Y.; Huppert, D. J. Phys. Chem. A 2011, 115, 7591.
[2] (a) Gould, E. A.; Popov, A. V.; Tolbert, L. M.; Presiado, I.; Erez, Y.; Huppert, D.; Solntsev, K. M. Phys. Chem. Chem. Phys. 2012. 14. 8964. (b) Thompson, W. H. J. Phys. Chem. B 2005, 109, 18201. (c) Gould, E. A.; Popov, A. V.; Tolbert, L. M.; Presiado, I.; Erez, Y.; Huppert, D.; Solntsev, K. M. Phys. Chem. Chem. Phys. 2012. 14. 8964. (d) Yi, P. G.; Liu, Z. J.; Wang, Z. X.; Hou, B.; Yu, X. Y.; Li, X. F. Acta Chim. Sinica 2012, 70, 27 (in Chinese). (易平贵, 刘峥军, 汪朝旭, 侯博, 于贤勇, 李筱芳, 化学学报, 2012, 70, 27.) (e) Yi, P. G.; Zhou, J. M.; Yu, X. Y.; Wang, Z. X.; Li, X. F.; Liu, Z. J.; Hou, B. Acta Chim. Sinica 2012, 70, 699 (in Chinese). (易平贵, 周继明, 于贤勇, 汪朝旭, 李筱芳, 刘峥军, 侯博, 化学学报, 2012, 70, 699.) (f) Yi, P. G.; Zhou, J. M.; Wang, Z. X.; Yu, X. Y.; Li, X. F.; Chen, J.; Liu, Z. J. Acta Chim. Sinica 2012, 70, 1645 (in Chinese). (易平贵, 周继明, 汪朝旭, 于贤勇, 李筱芳, 陈建, 刘峥军, 化学学报, 2012, 70, 1645.) (g) Yi, P. G.; Peng, H. L.; Wang, Z. X.; Yu, X. Y.; Li, X. F.; Liang, Y. H. Chin. J. Chem 2011, 29, 4, 650.
[3] (a) Cui, S.; Tachikawa, T.; Fujitsuka, M.; Majima, T. J. Phys. Chem. C 2011, 115, 1824. (b) Parvari, G.; Reany, O.; Keinan, E. Isr. J. Chem. 2011, 51, 646. (c) Halterman, R.; Moore, J.; Yip, W. J. Fluoresc. 2011, 21, 1467.
[4] (a) Fu, X. Z.; Huang, Y.; Tao, Z.; Xue, S. F.; Luo, C.; Ou, Y.; Zhang, J. X. Chin. J. Org. Chem. 2010, 30, 675 (in Chinese). (傅晓钟, 黄英, 陶朱, 薛赛凤, 罗春, 欧瑜, 张建新, 有机化学, 2010, 30, 675.) (b) Fan, Z.; Wang, J.; Huang, Y.; Xue, S.; Xiao, X.; Zhang, Y.; Zhu, Q.; Tao, Z. J. Inclusion Phenom. Macrocyclic Chem. 2012, 72, 213.
[5] (a) Prabhu, A.; Siva, S.; Sankaranarayanan, R.; Rajendiran, N. J. Fluoresc. 2010, 20, 43. (b) Lee, Y.; Kwon, O.; Park, H. J.; Franz, J.; Jang, D. J. Photochem. Photobiol. A 2008, 194, 105. (c) Kim, Y.; Yoon, M.; Kim, D. J. Photochem. Photobiol. A 2001, 138, 167.
[6] (a) Yi, P. G.; Wang, T.; Yu, X. Y.; Zhou, J. M.; Liu, R. H.; Wang, Z. X.; Zheng, B. S. Chin. J. Inorg. Chem. 2011, 27, 480 (in Chinese). (易平贵, 王涛, 于贤勇, 周继明, 刘容华, 汪朝旭, 郑柏树, 无机化学学报, 2011, 27, 480.) (b) Yi, P. G.; Wang, T.; Zhou, J. M.; Peng, H. L.; Li, X. F.; Yu, X. Y.; Wang, Z. X. Acta Chim. Sinica 2009, 67, 2803 (in Chinese). (易平贵, 王涛, 周继明, 彭洪亮, 李筱芳, 于贤勇, 汪朝旭, 化学学报, 2009, 67, 2803.) (c) Yi, P. G.; Yang, X. C.; Yu, X. Y; Liu, Z. J.; Liu, J.; Wang, Z. X. Chem. J. Chin. Univ. 2012, 33, 2657 (in Chinese). (易平贵, 阳习春, 于贤勇, 刘峥军, 刘金, 汪朝旭, 高等学校化学学报, 2012, 33, 2657.)
[7] Shaikh, M.; Dutta Choudhury, S.; Mohanty, J.; Bhasikuttan, A. C.; Nau, W. M.; Pal, H. Chem.-Eur. J. 2009, 15, 12362.
[8] (a) Hammond, P. R. J. Chem. Soc., Pak. 1964, 479. (b) Yang, D. K.; Zeng, Z. J.; Chen, M. J.; Fan, S. W.; Yang, Y.; Li, M.; Lei, C. Y.; Jiang, L. S. Acta Chim. Sinica 2012, 70, 65 (in Chinese). (杨登科, 曾志坚, 陈木娟, 潘绍武, 杨宇, 李媚, 雷春燕, 蒋腊生, 化学学报, 2012, 70, 65.)
[9] (a) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218. (b) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454.
[10] (a) Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Chem. Phys. Lett. 1998, 286, 253. (b) Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151.
[11] Benson, G. M.; Bleicher, K.; Chucholowski, A.; Dehmlow, H.; Grether, U.; Kuhn, B.; Martin, R. E.; Niesor, E. J.; Panday, N.; Richter, H.; Schuler, F.; Warot, X. M.; Wright, M.; Yang, M. US 7645785, 2010[Chem. Abstr. 2008, 148, 121703].
[12] Ge, J.; Xue, S.; Zhu, Q.; Tao, Z.; Zhang, J. J. Inclusion Phenom. Macrocyclic 2007, 58, 63.
[13] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh PA, 2003.

七元瓜环纳米腔限制环境下2-(3-乙酰胺基-2-吡啶基)苯并咪唑的激发态质子转移

Investigation of Excited-State Proton Transfer of 2-(3-Acetamido-2-pyridyl)benzimidazole in the Confined Nanocavity of Cucurbit[7]uril

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 6

Recommended Articles

Metrics

Comments

[1]	Yuetian Guo, Yongxin Pan, Lijun Tang. Progresses in Reactive Fluorescent Probes with Fused Aggregation- Induced Emission (AIE) and Excited State Intramolecular Proton Transfer (ESIPT) Structures [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1640-1650.
[2]	Wang Ruixianga, Lai Xiaojinga, Qiu Guanyinsheng, Liu Jinbiao. Recent Advances in Reaction-Based Excited State Intramolecular Proton Transfer (ESIPT) Fluorescence Probe [J]. Chin. J. Org. Chem., 2019, 39(4): 952-960.
[3]	Liu, Yu, Tang, Yongxing, Luo, Yueyang, Zhu, Yeting, Yang, Jin, Wei, Xinyu, Liu, Xiong, Zhao, Yunhui. Synthesis and Application of Fluorescent Probe Containing Barbitone Unit [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2980-2984.
[4]	Ma Tuo, Zhang Jin, Liu Longzhu, He Yun, Zhang Zunting. Synthesis and Characterization of a Visualization and Water-Soluble Fluorescent Probe for Al³⁺ [J]. Chin. J. Org. Chem., 2014, 34(9): 1780-1785.
[5]	Zhang Peng, Zhang Youming, Lin Qi, Yao Hong, Wei Taibao. Principle and the Research Progress of Fluorescent Chemosensors for Cations Recognition [J]. Chin. J. Org. Chem., 2014, 34(7): 1300-1321.
[6]	CAI Meng-Jun, CHEN Jian-Ding. A New Ultrasonic Synthetic Method for Proton Transfer Compound of 2,6-Pyridinedicarboxylic Acid and 2,6-Pyridinediamine [J]. Chin. J. Org. Chem., 2010, 30(07): 1076-1079.