超声促进两组分多彩发光体系分子聚集体的共组装及其对酸的响应行为

doi:10.6023/A12060270

化学学报 ›› 2012, Vol. 70 ›› Issue (19): 2016-2023.DOI: 10.6023/A12060270 上一篇下一篇

研究论文

超声促进两组分多彩发光体系分子聚集体的共组装及其对酸的响应行为

余旭东^a,b, 刘倩^a, 许秀芳^c, 兰海闯^a, 曹新华^a, 陈黎明^a, 刘斌^a, 易涛^a

a 复旦大学化学系上海 200433;
b 河北科技大学理学院石家庄 050080;
c 南开大学化学系天津 300071

投稿日期:2012-06-01 发布日期:2012-07-13
通讯作者: 易涛 E-mail:yitao@fudan.edu.cn
基金资助:
项目受国家自然科学基金(Nos. 91022021 and 30890141);973项目(No. 2009CB930400);教育部创新团队(No. IRT1117)和上海市重点学科(No. B108)资助.

Ultrasound Assisted Co-aggregation of a Two-component System with Multicolor Emission and Its Response to Acid

Yu Xudong^a,b, Liu Qian^a, Xu Xiufang^c, Lan Haichuang^a, Cao Xinhua^a, Chen Liming^a, Liu Bin^a, Yi Tao^a

a Department of Chemistry, Fudan University, Shanghai 200433;
b College of Science, Hebei University of Science and Technology, Shijiazhuang 050080;
c Department of Chemistry, Nankai University, Tianjin 300071

Received:2012-06-01 Published:2012-07-13
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 91022021 and 30890141), the National Basic Research Program of China (No. 2009CB930400), the Program for Innovative Research Team in University (No. IRT1117) and the Shanghai Leading Academic Discipline Project (No. B108).

文章分享

摘要/Abstract

设计合成了一种含凝胶因子和微晶的两组分凝胶体系, 由发蓝光的氨基酸衍生物和发红光的苊唑衍生物构成. 在超声和热的协同作用下, 可促进凝胶因子的羧基和微晶分子中的苊唑氮进行酸碱配位, 从而实现该两组分在分子聚集体层次的共组装. 两种化合物分别能发出蓝色和红色荧光, 便于我们通过共聚焦显微镜(CLSM)来直接观测其微观聚集行为. CLSM图片表明通过加热冷却的方法所获得的干凝胶其微观结构是由发红光的棒状微晶和发蓝光的纤维组成的混合体; 当通过一个预超声再加热-冷却的过程, 可以得到一种均匀的同时发射蓝光和红光的凝胶纤维聚集体. 结果表明, 超声和热的协同作用可以有效地促进分子间的聚集, 从而形成均相体系. 进一步, 我们通过超声诱导的分子间共聚集构建了微纳米层次上的多彩发光体系. 该体系发射光谱可以通过两种成分的混合比例来精确调控, 同时可以通过加入质子酸进一步调控. 与此同时, 酸的加入也诱导了两组分组装体发生由纤维向囊泡的形貌变化, 并伴随着凝胶向溶胶的宏观相态转变. 当加入碱后, 该溶胶可恢复为凝胶. 这种具有多重功能并易于调控的两组分凝胶在可视化分子识别、控制缓释、刺激响应和记忆材料等领域具有潜在应用价值.

关键词: 两组分凝胶, 超声, 共组装, 荧光, 酸响应

In this paper, a two-component gel/micro-crystal system including amino acid and imidazole-based derivatives with blue and red emission, respectively, is designed and obtained. The two emission colors are convenient for the study of the co-aggregation of the two molecules via double channel confocal laser scanning microscopy. The two-component system could response to ultrasound with the morphology change from the mixture of club-shaped microcrystals and helical fibers by a thermal process to homogenous fibers exposing to sonication. Further evidence for the co-aggregation of the two components was obtained from circular dichromism (CD), IR spectra and X-ray powder diffraction. The self-assembly process between the two components was also studied by optimized molecular geometry calculation. Moreover, the co-aggregation obtained by the sonication then heating-cooling process, could not be destroyed by repeated heating-cooling. The gel-sol process could be further repeated for many times, suggesting that the co-aggregated gel was thermal-stable. It can be deduced that sonication weakened the intermolecular interaction between congeneric molecules and promoted the intermolecular hydrogen bonding between the two components. The results indicate that cooperation of the sonication and thermal processes is an effective way to prohibit phase separation and to promote gelation in the gel/micro-crystal system. Thus, a light harvest system is achieved by co-aggregation of the two components at nanoscale by means of sonication. The emission color of these two-component gels can be tuned by changing the ratio of the two compounds. These gels are sensitive to acid, givingclear spectral variation, accompanied by a gel to sol transition. The morphology of the two-component system is changed from a fiber structure to vesicles without phase separation when responding to acid and metal ions. Moreover, both the gel state and the morphology can be reversed by further addition of alkali. This kind of multifunctional and tunable two-component gel should have potential applications on the fields of visible molecular recognition, controllable release, stimulus responsive and memory materials.

Key words: two-component gel, ultrasound, co-aggregation, fluorescence, acid response

引用此文

余旭东, 刘倩, 许秀芳, 兰海闯, 曹新华, 陈黎明, 刘斌, 易涛. 超声促进两组分多彩发光体系分子聚集体的共组装及其对酸的响应行为[J]. 化学学报, 2012, 70(19): 2016-2023.

Yu Xudong, Liu Qian, Xu Xiufang, Lan Haichuang, Cao Xinhua, Chen Liming, Liu Bin, Yi Tao. Ultrasound Assisted Co-aggregation of a Two-component System with Multicolor Emission and Its Response to Acid[J]. Acta Chimica Sinica, 2012, 70(19): 2016-2023.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Partridge, K. S.; Smith, D. K.; Dykes, G. M.; McGrail, P. T. Chem. Commun. 2001, 319; (b) Hirst, A. R.; Smith, D. K.; Harring-ton, J. P. Chem.-Eur. J. 2005, 11, 6552; (c) Hirst, A. R.; Smith, D. K.; Feiters, M. C.; Geurts, H. P. M. Langmuir 2004, 20, 7070; (d) Hirst, A. R.; Smith, D. K. Langmuir 2004, 20, 10851; (e) Hirst, A. R.; Smith, D. K.; Feiters, M. C.; Geurts, H. P. M. Chem.-Eur. J. 2004, 10, 5901; (f) Hirst, A. R.; Smith, D. K.; Feiters, M. C.; Geurts, H. P. M.; Wright, A. C. J. Am. Chem. Soc. 2003, 125, 9010; (g) Si-malou, O.; Xue, P.; Lu, R. Tetrahedron Lett. 2010, 51, 3685; (h) Suzuki, M.; Saito, H.; Hanabusa, K. Langmuir 2009, 25, 8579; (i) Zhou, Y.; Xu, M.; Yi, T.; Xiao, S.; Zhou, Z.; Li, F.; Huang, C. Langmuir 2007, 23, 202; (j) Yi, T.; Sada, K.; Sugiyasu, K.; Hatano, T.; Shinkai, S. Chem. Commun. 2003, 344.

[2] (a) Ajayaghosh, A.; Chithra, P.; Varghese, R. Angew. Chem., Int. Ed. 2007, 46, 230; (b) Suzuki, M.; Yumoto, M.; Shirai, H.; Hanabusa, K. Chem.-Eur. J. 2008, 14, 2133.

[3] (a) Ajayaghosh, A.; Praveen, V. K.; Vijayakumar, C.; George, S. J. Angew. Chem., Int. Ed. 2007, 46, 6260; (b) Shu, T.; Wu, J.; Lu, M.; Chen, L.; Yi, T.; Li, F.; Huang, C. J. Mater. Chem. 2008, 18, 886; (c) Bao, C.; Lu, R.; Jin, M.; Xue, P.; Tan, C.; Liu, G.; Zhao, Y. Org. Biomol. Chem. 2005, 3, 2508; (d) Babu, P.; Sangeetha, N. M.; Vijaykumar, P.; Maitra, U.; Rissanen, K.; Raju, A. R. Chem.-Eur. J. 2003, 9, 1922.

[4] (a) Liao, P.; Langloss, B. W.; Johnson, A. M.; Knudsen, E. R.; Tham, F. S.; Julian, R. R.; Hooley, R. J. Chem. Commun. 2010, 46, 4932; (b) Huang, S.; Li, X.; Shi, X.; Hou, H.; Fan, Y. T. J. Mater. Chem. 2010, 20, 5695; (c) Valente, C.; Choi, E.; Belowich, M. E.; Doonan, C. J.; Li, Q. W.; Gasa, T. B.; Botros, Y. Y.; Yaghi, O. M.; Stoddart, J. F. Chem. Commun. 2010, 46, 4911; (d) Weng, W.; Beck, J. B.; Jamieson, A. M.; Rowan, S. J. J. Am. Chem. Soc. 2006, 128, 11663; (e) Paoli, G. D.; D?olic, Z.; Rizzo, F.; Cola, L. D.; Vögtle, F.; Müller, W. M.; Richardt, G.; ?inic, M. Adv. Funct. Mater. 2007, 17, 821; (f) Hui, J. K.-H.; Yu, Z.; MacLachlan, M. J. Angew. Chem., Int. Ed. 2007, 46, 7980; (g) George, M.; Funkhouser, G. P.; Terech, P. R.; Weiss, G. Langmuir 2006, 22, 7885.

[5] (a) Molla, M. R.; Das, A.; Ghosh, S. Chem.-Eur. J. 2010, 16, 10084; (b) Das, R. K.; Banerjee, S.; Raffy, G.; Del Guerzo, A.; Desvergne, J.-P.; Maitra, U. J. Mater. Chem. 2010, 20, 7227; (c) Friggeri, A.; Gronwald, O.; van Bommel, K. J. C.; Shinkai, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 10754; (d) Rao, K. V.; Jayaramulu, K.; Maji, T. K.; George, S. J. Angew. Chem., Int. Ed. 2010, 49, 4218.

[6] (a) Wang, W. C.; Du, C.; Bi, H.; Sun, Y. H.; Wang, Y.; Mauser, C.; Como, E. D.; Fuchs, H.; Chi, L. F. Adv. Mater. 2010, 22, 2764; (b) Nalluri, S. K. M.; Ravoo, B. J. Angew. Chem., Int. Ed. 2010, 49, 5371; (c) Mahesh, S.; Thirumalai, R.; Yagai, S.; Kitamura, A.; Ajayaghosh, A. Chem. Commun. 2009, 5984; (d) Chen, Q.; Zhang, D.; Zhang, G.; Yang, X.; Feng, Y.; Fang, Q.; Zhu, D. B. Adv. Funct. Mater. 2010, 20, 3244; (e) Shumburo, A.; Biewer, M. C. Chem. Mater. 2002, 14, 3745; (f) Li, J. L.; Liu, X. Y. Adv. Funct. Mater. 2010, 20, 3196; (g) Wang, C.; Chen, Q.; Sun, F.; Zhang, D.; Zhang, G.; Huang, Y.; Zhao, R.; Zhu, D. J. Am. Chem. Soc. 2010, 132, 3092.

[7] (a) Mukhopadhyay, P.; Iwashita, Y.; shirakawa, M.; Kawano, S.; Fujita, N.; Shinkai, S. Angew. Chem., Int. Ed. 2006, 45, 1592; (b) Ajayaghosh, A.; Varghese, R.; Mahesh, S.; Praveen, V. K. Angew. Chem., Int. Ed. 2006, 45, 7729; (c) Palmans, A. R. A.; Meijer, E. W. Angew. Chem., Int. Ed. 2007, 46, 8948.

[8] (a) Naota, T.; Koori, H. J. Am. Chem. Soc. 2005, 127, 9324; (b) Wang, C.; Zhang, D. Q.; Zhu, D. B. J. Am. Chem. Soc. 2005, 127, 16372; (c) Paulusse, J. M. J.; Sijbesma, R. P. Angew. Chem., Int. Ed. 2006, 45, 2334; (d) Bardelang, D. Soft Matter 2009, 5, 1969; (f) Cravotto, G.; Cintas, P. Chem. Soc. Rev. 2009, 38, 2684.

[9] Richards, W. T.; Loomis, A. L. J. Am. Chem. Soc. 1927, 49, 3086.

[10] Donaldson, D. J.; Farrington, M. D.; Kruus, P. J. Phys. Chem. 1979, 83, 3130.

[11] Petrier, C.; Jeunet, A.; Luche, J.-L.; Reverdy, G. J. Am. Chem. Soc. 1992, 114, 3148.

[12] Kitazume, T.; Ishikawa, N. J. Am. Chem. Soc. 1985, 107, 5186.

[13] (a) Wu, J.; Yi, T.; Shu, T.; Yu, M.; Zhou, Z.; Xu, M.; Zhou, Y.; Zhang, H.; Han, J.; Li, F.; Huang, C. Angew. Chem., Int. Ed. 2008, 47, 1063; (b) Wu, J.; Yi, T.; Xia, Q.; Zou, Y.; Liu, F.; Dong, J.; Shu, T.; Li, F.; Huang, C. Chem.-Eur. J. 2009, 15, 6234.

[14] Yu, X.; Liu, Q.; Wu, J.; Zhang, M.; Cao, X.; Zhang, H.; Wang, Q.; Chen, L.; Yi, T. Chem.-Eur. J. 2010, 16, 9099.

[15] Anderson, K. M.; Day, G. M.; Paterson, M. J.; Byrne, P.; Clarke, N.; Steed, J. W. Angew. Chem., Int. Ed. 2008, 47, 1058.

[16] Chen, L.; Wu, J.; Shu, T.; Xu, M.; Zhang, M.; Yi, T. Langmuir 2009, 25, 8434.

[17] Zhang, M.; Yu, M.; Li, F.; Zhu, M.; Li, M.; Gao, Y.; Li, L.; Liu, Z.; Zhang, J.; Zhang, D.; Yi, T. Huang, C. J. Am. Chem. Soc. 2007, 129, 10322.

[18] (a) Weiss, M. J. Am. Chem. Soc. 1952, 74, 5193; (b) White, D. M. J. Org. Chem. 1970, 35, 2452.

超声促进两组分多彩发光体系分子聚集体的共组装及其对酸的响应行为

Ultrasound Assisted Co-aggregation of a Two-component System with Multicolor Emission and Its Response to Acid

PDF

可视化

被引次数

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	车飞达, 赵晓茗, 张馨, 丁琪, 王昕, 李平, 唐波. 抑郁症相关活性分子的荧光成像^★[J]. 化学学报, 2023, 81(9): 1255-1264.
[2]	葛凤洁, 张开志, 曹清鹏, 徐慧, 周涛, 张文浩, 班鑫鑫, 张晓波, 李娜, 朱鹏. 柔性芴基嵌段型延迟荧光二聚体的设计、合成及电致发光性能[J]. 化学学报, 2023, 81(9): 1157-1166.
[3]	王一诺, 邵世洋, 王利祥. 窄谱带多重共振有机高分子荧光材料研究进展^★[J]. 化学学报, 2023, 81(9): 1202-1214.
[4]	武虹乐, 郭锐, 迟涵文, 唐永和, 宋思睿, 葛恩香, 林伟英. 喹啉基粘度荧光探针的合成及其检测应用[J]. 化学学报, 2023, 81(8): 905-911.
[5]	王晓, 王星文, 肖乐辉. 单分子荧光成像研究单颗粒纳米催化机制[J]. 化学学报, 2023, 81(8): 1002-1014.
[6]	罗楚文, 孔超颖, 汤朝晖. 超声化学在生物医学中应用的研究进展^★[J]. 化学学报, 2023, 81(7): 836-842.
[7]	郑文山, 高冠斌, 邓浩, 孙涛垒. Ag₂Se@Ag₂S核壳量子点的室温合成及其近红外荧光性能优化[J]. 化学学报, 2023, 81(7): 763-770.
[8]	刘振宇, 饶俊峰, 祝守加, 王兵洋, 余帆, 冯全友, 解令海. 溶液加工型自主体热活化延迟荧光材料的研究进展[J]. 化学学报, 2023, 81(7): 820-835.
[9]	王银凤, 李猛, 陈传峰. 基于手性三蝶烯的红光热激活延迟荧光聚合物及其有机发光二极管研究^★[J]. 化学学报, 2023, 81(6): 588-594.
[10]	梁攀, 张宏淑, 黄宏升, 李飒英, 张笑恬, 王英, 李连庆, 刘志宏. 一种高效窄带蓝色荧光粉Ba₃Y₂B₆O₁₅:Bi³⁺及其应用研究[J]. 化学学报, 2023, 81(4): 371-380.
[11]	吕鑫, 吴仪, 张勃然, 郭炜. 过氧化氢激活型近红外氟硼二吡咯光敏剂的设计、合成及光动力治疗研究[J]. 化学学报, 2023, 81(4): 359-370.
[12]	张少秦, 李美清, 周中军, 曲泽星. 多共振热激活延迟荧光过程的理论研究[J]. 化学学报, 2023, 81(2): 124-130.
[13]	贾彦荣, 徐凯, 赵彦英, 倪华钢, 吴滢, 夏敏. 推拉电子基团区域异构苯并咪唑的发射行为与力致荧光变色性能研究[J]. 化学学报, 2023, 81(12): 1716-1723.
[14]	黄艳琴, 栗丽君, 杨书培, 张瑞, 刘兴奋, 范曲立, 黄维. HA-AuNPs/FDF用于透明质酸酶的高灵敏检测、肿瘤靶向细胞荧光成像和光疗[J]. 化学学报, 2023, 81(12): 1687-1694.
[15]	贺晓梦, 袁方, 张素雅, 张健健. 基于尼罗红类ONOO^–近红外荧光探针的开发及其成像应用[J]. 化学学报, 2023, 81(11): 1515-1521.