Pyrenyl Peripheral-Decorated Polyamidoamine Dendrimer for Fluorescent Temperature Detection in Aqueous Phase

doi:10.6023/A16100544

Acta Chim. Sinica ›› 2017, Vol. 75 ›› Issue (1): 99-104.DOI: 10.6023/A16100544 Previous Articles Next Articles

Special Issue: 有机光化学

Article

基于芘修饰树枝形聚合物的水相温敏荧光传感体系

秦天依^a,b, 曾毅^a,b, 陈金平^a, 于天君^a, 李嫕^a,b

a 中国科学院理化技术研究所光化学转换与功能材料重点实验室北京 100190;
b 中国科学院大学北京 100049

投稿日期:2016-10-13 修回日期:2016-10-27 发布日期:2016-11-24
通讯作者: 曾毅,E-mail:zengyi@mail.ipc.ac.cn;李嫕,E-mail:yili@mail.ipc.ac.cn E-mail:zengyi@mail.ipc.ac.cn;yili@mail.ipc.ac.cn
基金资助:
项目受国家自然科学基金（No.21233011）和973项目（2013CB834703 and 2013CB834505）资助.

Pyrenyl Peripheral-Decorated Polyamidoamine Dendrimer for Fluorescent Temperature Detection in Aqueous Phase

Qin Tianyi^a,b, Zeng Yi^a,b, Chen Jinping^a, Yu Tianjun^a, Li Yi^a,b

a Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190;
b University of Chinese Academy of Sciences, Beijing 100049

Received:2016-10-13 Revised:2016-10-27 Published:2016-11-24
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21233011) and 973 Program (2013CB834703 and 2013CB834505).

1. Pyrenyl Peripheral-Decorated Polyamidoamine Dendrimer for Fluorescent Temperature Detection in Aqueous Phase.PDF(660KB)

Abstract

A protonated polyamidoamine (PAMAM) dendrimer of generation 2 with pyrenyl attached to its periphery (G2 PAMAM-PyH) was designed and synthesized. G2 PAMAM-Py was synthesized by a condensation of the terminal amino group of the PAMAM dendrimer and the aldehyde group of 1-pyrenecarboxaldehyde followed by a reduction of Schiff base through "one pot" reaction. G2 PAMAM-Py was further protonated by adding HCl, giving the target product G2 PAMAM-PyH. The structure of G2 PAMAM-PyH was characterized by NMR, FTIR, and MS. The functionalization extent of the peripheral amino groups of PAMAM by pyrenyl is 100% according to the ¹H NMR and UV-visible spectra. The amphiphilic G2 PAMAM-PyH is soluble in water with a critical aggregation concentration of 3.3×10^-7 mol·dm^-3. Absorption, dynamic light scattering (DLS), and transmission electronic microscopy (TEM) studies demonstrate that G2 PAMAM-PyH exists as vesicle with a bilayer membrane and an average hydrodynamic diameter of ca. 184 nm in aqueous phase. G2 PAMAM-PyH in aqueous phase exhibits dual fluorescence, pyrenyl monomer and excimer emission. The pyrenyl monomer fluorescence increases slightly and the pyrenyl excimer emission decreases monotonically upon temperature raising from 1 to 70℃. Meanwhile, the fluorescence color changes from green (low temperature) to blue (high temperature). The monomer emission enhancement is mainly attributed to less formation of excimer when rising temperature. The fluorescence intensity ratio of pyrenyl excimer to pyrenyl monomer (I_{495 nm}/I_{398 nm}) changes with varying temperature recoverably, and the relationship between I_{495 nm}/I_{398 nm} and temperature can be expressed as I_{495 nm}/I_{398 nm}=28.23-0.68t+3.21×10^-3t²+1.83×10^-5t³. The accuracy for the measurement of the temperature is better than 0.9℃ in the temperature range of 1~70℃, facilitating in situ gradient temperature measurement. The temperature gradient of aqueous phase in a glass tube is investigated by using G2 PAMAM-PyH, which is consistent with the detection result by using a thermocouple meter. This study provides a potential strategy for developing fluorescent temperature sensing system.

Key words: temperature detection, fluorescence sensor, polyamidoamine dendrimer, pyrene

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Qin Tianyi, Zeng Yi, Chen Jinping, Yu Tianjun, Li Yi. Pyrenyl Peripheral-Decorated Polyamidoamine Dendrimer for Fluorescent Temperature Detection in Aqueous Phase[J]. Acta Chim. Sinica, 2017, 75(1): 99-104.

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[1] (a) Wolfbeis, O. S. Adv. Mater. 2008, 20, 3759;
(b) Mesli, A.; Dobaczewski, L.; Nielsen, K. B.; Kolkovsky, V.; Petersen, M. C.; Larsen, A. N. Phys. Rev. B 2008, 78, 165202;
(c) Uchiyama, S.; de Silva, A. P.; Iwai, K. J. Chem. Educ. 2006, 83, 720;
(d) Kucsko, G.; Maurer, P. C.; Yao, N. Y.; Kubo, M.; Noh, H. J.; Lo, P. K.; Park, H.; Lukin, M. D. Nature 2013, 500, 54-U71.
[2] (a) Childs, P. R. N.; Greenwood, J. R.; Long, C. A. Rev. Sci. Instrum. 2000, 71, 2959;
(b) Seyedyagoobi, J. Rev. Sci. Instrum. 1991, 62, 249.
[3] (a) Lee, T. W.; Hegde, N. Combust. Flame 2005, 142, 314;
(b) Chung, K.; Cho, J. K.; Park, E. S.; Breedveld, V.; Lu, H. Anal. Chem. 2009, 81, 991.
[4] (a) Ring, E. F. J. Infrared Phys. Techn. 2007, 49, 297;
(b) Grattan, K. T. V.; Palmer, A. W. Rev. Sci. Instrum. 1985, 56, 1784;
(c) Dabiri, D. Exp. Fluids 2009, 46, 191.
[5] (a) Wang, X. D.; Wolfbeis, O. S.; Meier, R. J. Chem. Soc. Rev. 2013, 42, 7834;
(b) Brites, C. D. S.; Lima, P. P.; Silva, N. J. O.; Millan, A.; Amaral, V. S.; Palacio, F.; Carlos, L. D. Nanoscale 2012, 4, 4799;
(c) Song, Q. S.; Yang, S. S.; Sheng, R.; Li, T. Acta Chim. Sinica 2014, 72, 89 (in Chinese). (宋秋生, 杨森森, 盛锐, 李谭, 化学学报, 2014, 72, 89.)
[6] (a) Liu, J.; Guo, X. D.; Hu, R.; Xu, J.; Wang, S. Q.; Li, S. Y.; Li, Y.; Yang, G. Q. Anal. Chem. 2015, 87, 3694;
(b) Liu, X.; Li, S. Y.; Feng, J.; Li, Y.; Yang, G. Q. Chem. Commun. 2014, 50, 2778;
(c) Okabe, K.; Inada, N.; Gota, C.; Harada, Y.; Funatsu, T.; Uchiyama, S. Nat. Commun. 2012, 3, 705;
(d) Feng, J.; Tian, K. J.; Hu, D. H.; Wang, S. Q.; Li, S. Y.; Zeng, Y.; Li, Y.; Yang, G. Q. Angew. Chem.-Int. Ed. 2011, 50, 8072;
(e) Feng, J.; Xiong, L.; Wang, S. Q.; Li, S. Y.; Li, Y.; Yang, G. Q. Adv. Funct. Mater. 2013, 23, 340;
(f) Ebrahimi, S.; Akhlaghi, Y.; Kompany-Zareh, M.; Rinnan, A. ACS Nano 2014, 8, 10372;
(g) Zhegalova, N. G.; Dergunov, S. A.; Wang, S. T.; Pinkhassik, E.; Berezin, M. Y. Chem.-Eur. J. 2014, 20, 10292;
(h) Hu, X. L.; Li, Y.; Liu, T.; Zhang, G. Y.; Liu, S. Y. ACS Appl. Mater. Interfaces 2015, 7, 15551;
(i) Song, Q. S.; Zhou, W.; Wu, X. M.; Wu, F. Acta Chim. Sinica 2016, 74, 435 (in Chinese). (宋秋生, 周稳, 吴新民, 吴凡, 化学学报, 2016, 74, 435.)
[7] Ross, D.; Gaitan, M.; Locascio, L. E. Anal. Chem. 2001, 73, 4117.
[8] Ye, F.; Wu, C.; Jin, Y.; Chan, Y.-H.; Zhang, X.; Chiu, D. T. J. Am. Chem. Soc. 2011, 133, 8146.
[9] Ozawa, A.; Shimizu, A.; Nishiyabu, R.; Kubo, Y. Chem. Commun. 2015, 51, 118.
[10] (a) Kojima, C.; Irie, K.; Tada, T.; Tanaka, N. Biopolymers 2014, 101, 603;
(b) Cakara, D.; Kleimann, J.; Borkovec, M. Macromolecules 2003, 36, 4201.
[11] (a) Zeng, Y.; Li, Y. Y.; Li, M.; Yang, G. Q.; Li, Y. J. Am. Chem. Soc. 2009, 131, 9100;
(b) Zhang, X. H.; Zeng, Y.; Yu, T. J.; Chen, J. P.; Yang, G. Q.; Li, Y. Langmuir 2014, 30, 718;
(c) Liu, X. Y.; Zeng, Y.; Liu, J.; Li, P.; Zhang, D. S.; Zhang, X. H.; Yu, T. J.; Chen, J. P.; Yang, G. Q.; Li, Y. Langmuir 2015, 31, 4386;
(d) Li, P.; Zeng, Y.; Chen, J. P.; Li, Y. Y.; Li, Y. Acta Chim. Sinica 2012, 70, 1611 (in Chinese). (李鹏, 曾毅, 陈金平, 李迎迎, 李嫕, 化学学报, 2012, 70, 1611.)
[12] Zeng, Y.; Li, Y. Y.; Yuan, Z.; Li, Y. Acta Chim. Sinica 2009, 67, 2714 (in Chinese). (曾毅, 李迎迎, 袁钊, 李嫕, 化学学报, 2009, 67, 2714.)
[13] (a) Baker, G. A.; Baker, S. N.; McCleskey, T. M. Chem. Commun. 2003, 2932;
(b) Lou, J. F.; Hatton, T. A.; Laibinis, P. E. Anal. Chem. 1997, 69, 1262.
[14] Sehgal, R. K.; Kumar, S. Org. Prep. Proced. Int. 1989, 21, 223.

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基于芘修饰树枝形聚合物的水相温敏荧光传感体系

Pyrenyl Peripheral-Decorated Polyamidoamine Dendrimer for Fluorescent Temperature Detection in Aqueous Phase

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