Citation: CHEN Zhong-Xiu, CAO Chen, DENG Shao-Ping. Chaotrope-Assisted Color Visualization Mechanism and Thermodynamics Involved in Molecular Recognition of Melamine by Bolaamphiphiles Embedded in Polydiacetylene Vesicles[J]. Acta Physico-Chimica Sinica, ;2012, 28(06): 1320-1328. doi: 10.3866/PKU.WHXB201204064 shu

Chaotrope-Assisted Color Visualization Mechanism and Thermodynamics Involved in Molecular Recognition of Melamine by Bolaamphiphiles Embedded in Polydiacetylene Vesicles

1.
1. Department of Applied Chemistry, Zhejiang ngshang University, Hangzhou 310035, P. R. China;
2. Sensory Science Laboratory, Zhejiang ngshang University, Hangzhou 310035, P. R. China

Received Date: 28 January 2012
Available Online: 6 April 2012
Fund Project: 国家自然科学基金(20973155)资助项目 (20973155)

The interaction between melamine and 1,12-diaminododecanediorotate (DDO), a bolaamphiphile bearing molecular recognition sites for amine functional groups, was transformed into visible color changes using polymerized 2,4-tricosadiynoic acid (TCDA) vesicles. TCDA was found to be more sensitive than other polydiacetylene vesicles with various alkane chain-lengths in reporting the molecular recognition event. Colorimetric changes occurred as a result of modifications in the conjugated backbone of TCDA triggered by changes in the chemical environment associated with the recognition process. To better understand this mechanism, the influence of melamine on the thermotropic behavior of polydiacetylene vesicles and the thermodynamics were investigated via differential scanning calorimetry (DSC). It was found that the phase transitions of both TCDA and DDO/TCDA vesicles were shifted to higher temperatures when melamine was present, and that the magnitude of this shift increased as the melamine levels were raised. Color changes associated with the molecular recognition process were only observed with the unaided eye when melamine was introduced at levels well in excess of those theoretically required. Using sucrose and urea as model kosmotropic and chaotropic compounds, respectively, the effect of such solutes on the phase transition of polydiacetylene vesicles and equilibrium energetics of the molecular recognition were examined. Results indicate that the excess melamine likely behaves as a chaotrope in the colloid. In combination with the multipoint hydrogen bond formation between melamine and DDO, these effects are responsible for the blue-red color transition of the DDO/TCDA vesicles. Identification of this chaotrope-assisted color visualization mechanism for PDA vesicles provides new insights into the Hofmeister series effect on the conformation change of conjugated polymers.
- Molecular recognition,
- Melamine,
- Chaotrope,
- Polydiacetylene vesicle,
- Differential scanning calorimetry
1. [1]
  (1) Okada, S.; Peng, S.; Spevak, W.; Charych, D. Accounts Chem. Res. 1998, 31, 229. doi: 10.1021/ar970063v
2. [2]
  (2) Ahn, D. J.; Kim, J. M. Accounts Chem. Res. 2008, 41, 805. doi: 10.1021/ar7002489
3. [3]
  (3) Charych, D. H.; Nagy, J. O.; Spevak, W.; Bednarski, M. D. Science 1993, 261, 585. doi: 10.1126/science.8342021
4. [4]
  (4) Ma, Z. F.; Li, J. R.; Liu, M. H.; Cao, J.; Zou, Z. Y.; Tu, J.; Jiang L. J. Am. Chem. Soc. 1998, 120, 12678. doi: 10.1021/ja982663a
5. [5]
  (5) Kolusheva, S.; Katz, R. K. M.; Jelinek, R. J. Am. Chem. Soc. 2001, 123, 417. doi: 10.1021/ja0034139
6. [6]
  (6) Jaworski, J.; Yokoyama, K.; Zueger, C.; Chung, W. J.; Lee, S. W.; Majumdar, A. Langmuir 2011, 27, 3180. doi: 10.1021/la104476p
7. [7]
  (7) Sigal-Batikoff, I.; Konovalov, O.; Singh, A.; Berman, A. Langmuir 2010, 26, 16424. doi: 10.1021/la102166k
8. [8]
  (8) Mittapalli, G. K.; Osornio, Y. M.; Guerrero, M. A.; Reddy, K. R.; Krishnamurthy, R.; Eschenmoser, A. Angew. Chem. Int. Edit. 2007, 46, 2478. doi: 10.1002/anie.200603209
9. [9]
  (9) Ma, M.; Bong, D. Langmuir 2011, 27, 8841 and references therein.
10. [10]
  (10) Chen, Z. X.; Su, X. X.; Deng, S. P. J. Phys. Chem. B 2011, 115, 1798. doi: 10.1021/jp106385x
11. [11]
  (11) Potisatityuenyong, A.; Rojanathanes, R.; Tumcharern, G.; Sukwattanasinitt, M. Langmuir 2008, 24, 4461. doi: 10.1021/la800354q
12. [12]
  (12) Cheng, Q.; Stevens, R. C. Langmuir 1998, 14, 1974. doi: 10.1021/la980185b
13. [13]
  (13) Huo, Q.; Russell, K. C.; Leblanc, R. M. Langmuir 1999, 15, 3972. doi: 10.1021/la990025f
14. [14]
  (14) Song, J.; Cheng, Q.; Kopta, S.; Stevens, R. C. J. Am. Chem. Soc. 2001, 123, 3205. doi: 10.1021/ja0035046
15. [15]
  (15) Charoenthai, N.; Pattanatornchai, T.; Wacharasindhu, S.; Sukwattanasinitt, M.; Traiphol, R. J. Colloid Interface Sci. 2011, 360, 565. doi: 10.1016/j.jcis.2011.04.109
16. [16]
  (16) Kolusheva, S.; Wachtel, E.; Jelinek, R. J. Lipid Res. 2003, 44, 65. doi: 10.1194/jlr.M200136-JLR200
17. [17]
  (17) Pires, A. C. S.; Soares, N. F. F.; da Silva, L. H. M.; da Silva, M. C. H.; Mageste, A. B.; Soares, R. F.; Teixeira, A. V. N. C.; Andrade, N. J. J. Phys. Chem. B 2010, 114, 13365. doi: 10.1021/jp105604t
18. [18]
  (18) Pang, J.; Yang, L.; McCaughey, B. F.; Peng, H.; Ashbaugh, H. S.; Brinker, C. J.; Lu, Y. J. Phys. Chem. B 2006, 110, 7221. doi: 10.1021/jp060309q
19. [19]
  (19) Wang, X.; Sandman, D. J.; Chen, S.; Gido, S. P. Macromolecules 2008, 41, 773. doi: 10.1021/ma070820x
20. [20]
  (20) Ahn, D. J.; Chae, E. H.; Lee, G. S.; Shim, H. Y.; Chang, T. E.; Ahn, K. D.; Kim, J. M. J. Am. Chem. Soc. 2003, 125, 8976. doi: 10.1021/ja0299001
21. [21]
  (21) Wu, S.; Niu, L.; Shen, J.; Zhang, Q.; Bubeck, C. Macromolecules 2009, 42, 362. doi: 10.1021/ma801709n
22. [22]
  (22) Dunstan, D. E.; Hill, E. K.; Wei, Y. Macromolecules 2004, 37, 1663. doi: 10.1021/ma030413v
23. [23]
  (23) Su,Y. L.; Li, J. R.; Jiang, L.; Cao, J. J. Colloid Interface Sci. 2005, 284, 114. doi: 10.1016/j.jcis.2004.10.003
24. [24]
  (24) Zhong, L.; Jiao, T.; Liu, M. J. Phys. Chem. B 2009, 113, 8867. doi: 10.1021/jp902822q
25. [25]
  (25) Su, Y. L.; Li, J. R.; Jiang, L. Colloids and Surfaces A: Physicochem. Eng. Aspects. 2005, 257-258, 25.
26. [26]
  (26) Chen, X.; Lee, J.; Jou, M. J.; Kim, J. M.; Yoon, J. Chem. Commun. 2009, 3434.
27. [27]
  (27) Thongmalai, W.; Eaidkong, T.; Ampornpun, S.; Mungkarndee, R.; Tumcharern, G.; Sukwattanasinitt, M.; Wacharasindhu, S. J. Mater. Chem. 2011, 21, 16391. doi: 10.1039/c1jm12795k
28. [28]
  (28) Lee, J.; Jeong, E. J.; Kim, J. Chem. Commun. 2011, 47, 358. doi: 10.1039/c0cc02183k
29. [29]
  (29) Sturtevant, J. M. Proc. Natl. Acad. Sci. U. S. A. 1982, 79, 3963. doi: 10.1073/pnas.79.13.3963
30. [30]
  (30) Mabrey-Gaud, S. Liposomes: From Physical Structure to Therapeutic Applications; Knight Ed.; Elsevier, North-Holland Biomedical Press: Amsterdam, 1981.
31. [31]
  (31) Barenholz, Y.; Bombelli, C.; Bonicelli, M. G.; di Profio, P.; Giansanti, L.; Mancini, G.; Pascale, F. J. Colloid Interface Sci. 2011, 356, 46. doi: 10.1016/j.jcis.2010.11.062
32. [32]
  (32) Schild, H. G.; Tirrel, D. A. J. Phys. Chem. 1990, 94, 4352. doi: 10.1021/j100373a088
33. [33]
  (33) Otake, K.; Inomata, H.; Kono, M.; Saito, S. Macromolecules 1990, 23, 283. doi: 10.1021/ma00203a049
34. [34]
  (34) Vecchio, P. D.; Graziano, G.; Granata, V.; Barone, G.; Mandrich, L.; Manco, G.; Rossi, M. Biochemistry 2002, 41, 1364. doi: 10.1021/bi011146t
35. [35]
  (35) Das, A.; Mukhopadhyay, C. J. Phys. Chem. B 2009, 113, 12816. doi: 10.1021/jp906350s
36. [36]
  (36) Nozaki, Y.; Tanford, C. J. Biol. Chem. 1963, 238, 4074.
37. [37]
  (37) Bianco, C. L.; Schneider, C. S.; Santonicola, M.; Lenhoff, A. M.; Kaler, E. W. Ind. Eng. Chem. Res. 2011, 50, 85. doi: 10.1021/ie101011v
38. [38]
  (38) Nostro, P. L.; Ninham, B. W.; Fratoni, L.; Palma, S.; Manzo, R. H.; Allemandi, D.; Baglioni, P. Langmuir 2003, 19, 3222. doi: 10.1021/la026807h
39. [39]
  (39) Yang, M.; Liu, C.; Li, Z.; Gao, G.; Liu, F. Macromolecules 2010, 43, 10645. doi: 10.1021/ma1022555
40. [40]
  (40) Ibarra-Molero, B.; Makhatadze, G. I.; Matthews, C. R. Biochemistry 2001, 40, 719. doi: 10.1021/bi001438e
41. [41]
  (41) Shechter, I.; Ramon, O.; Portnaya, I.; Paz, Y.; Livney, Y. D. Macromolecules 2010, 43, 480.
42. [42]
  (42) Alexandridis, P.; Holzwarth, J. F. Langmuir 1997, 13, 6074. doi: 10.1021/la9703712
43. [43]
  (43) Jones, G.; Dole, M. J. Am. Chem. Soc. 1929, 51, 2950. doi: 10.1021/ja01385a012
44. [44]
  (44) Amar-Yuli, I.; Aserin, A.; Garti, N. J. Phys. Chem. B 2008, 112, 10171. doi: 10.1021/jp802737k
1. [1]
  Yuanyuan Lian , Qingzhe Dong , Dashuang Wang , Lin Wang , Shuangshuang Liu , Yan Jiang , Nannan Wu . 近红外响应型多功能三聚氰胺泡沫的制备及其抗菌、电磁屏蔽性能研究. Acta Physico-Chimica Sinica, 2026, 42(11): 100352-. doi: 10.1016/j.actphy.2026.100352
2. [2]
  Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382
3. [3]
  Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . Green H₂O₂ synthesis via melamine-foam supported S-scheme Cd_0.5Zn_0.5In₂S₄/S-doped carbon nitride heterojunction: synergistic interfacial charge transfer and local photothermal effect. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-0. doi: 10.1016/j.actphy.2025.100093
4. [4]
  Jing Yan , Zenan Zhang , Dongwei Ma , Xinyi Zhang , Zhuodong Ye , Xuefang Chen . Melamine-assisted topotactic transformation of MOFs into needle-like α-MoC/β-Mo₂C for high-performance electromagnetic wave absorption and corrosion resistance. Acta Physico-Chimica Sinica, 2026, 42(9): 100328-0. doi: 10.1016/j.actphy.2026.100328
5. [5]
  Ziwen Lei , Mingyin Liu , Jiayi Shi , Yahan Shan , Qi Zhang . 当超分子二肽遇上酸碱指示剂：热响应水凝胶的智能可视化. University Chemistry, 2026, 41(8): 210-219. doi: 10.12461/PKU.DXHX202508014
6. [6]
  Tianrong Zhu , Fan Yu , Yuhang Liu , Haiyi Xu , Tingting Ma , Ming Li , Yuhang Xue , Yazhen Wang , Aihua Li , Biao Xiao , Xiaolun Peng . Intelligent Visualization, Precise Iodometry: Color Recognition-based Indirect Iodometric Method for Copper Determination. University Chemistry, 2026, 41(1): 264-275. doi: 10.12461/PKU.DXHX202503096
7. [7]
  Shuyu Liu , Xiaomin Sun , Bohan Song , Gaofeng Zeng , Bingbing Du , Chongshen Guo , Cong Wang , Lei Wang . Design and Fabrication of Phospholipid-Vesicle-based Artificial Cells towards Biomedical Applications. University Chemistry, 2024, 39(11): 182-188. doi: 10.12461/PKU.DXHX202404113
8. [8]
  Yubin Ding , Yanlin Fu , Ruiyue Hu , Huali Wan , Jiaxin Yu , Lei Wu . 创新实验——AIE分子聚集态调控及其糖胺聚糖模式识别应用. University Chemistry, 2026, 41(8): 331-338. doi: 10.12461/PKU.DXHX202507084
9. [9]
  Qiaorong RU . Synthesis and characterization of tripyridine functionalized polyionic liquid luminescent materials. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 111-119. doi: 10.11862/CJIC.20250121
10. [10]
  Senqiang Zhu , Ruohan Li , Yujia Yang , Jinzhi Liao , Rui Liu . 聚光成辉——Suzuki偶联反应高效制备聚集诱导发射荧光分子及其潜指纹识别应用. University Chemistry, 2026, 41(5): 109-119. doi: 10.12461/PKU.DXHX202511066
11. [11]
  Yaping Li , Sai An , Aiqing Cao , Shilong Li , Ming Lei . The Application of Molecular Simulation Software in Structural Chemistry Education: First-Principles Calculation of NiFe Layered Double Hydroxide. University Chemistry, 2025, 40(3): 160-170. doi: 10.12461/PKU.DXHX202405185
12. [12]
  Jiaxin Su , Jiaqi Zhang , Shuming Chai , Yankun Wang , Sibo Wang , Yuanxing Fang . Optimizing Poly(heptazine imide) Photoanodes Using Binary Molten Salt Synthesis for Water Oxidation Reaction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408012-0. doi: 10.3866/PKU.WHXB202408012
13. [13]
  Huiying ZHANG , Ping LI , Weixia DONG , Zhiwen HU , Qifu BAO , Qizheng DONG , Mingmin BAI , Wenqi LI . Photocatalytic performance of spheroidal nano Bi₄Ti₃O₁₂ prepared by surfactant-assisted hydrothermal reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 551-561. doi: 10.11862/CJIC.20250269
14. [14]
  Xing Yan , Yetai Cheng , Yixun Shu , Luyao Yang , Weidong Wang , Xinlu Bai , Ya-Nan Chen , Hao Lu , Zhishan Bo , Yahui Liu . Highly efficient and stable organic solar cells based on dimeric non-fused ring acceptors as the third component. Acta Physico-Chimica Sinica, 2026, 42(7): 100228-0. doi: 10.1016/j.actphy.2025.100228
15. [15]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
16. [16]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
17. [17]
  Meng Li , Haiyan Tan , Wenjun Zhu . Three-motif molecular junction photocatalysts with long-lived charge carriers for H₂O₂ production. Acta Physico-Chimica Sinica, 2026, 42(6): 100257-0. doi: 10.1016/j.actphy.2026.100257
18. [18]
  Songmei Ma , Ying Zhang , Gang Liu , Wenlong Xu . Comprehensive Experiment Teaching Exploration and Practice in Polymeric Materials Integrating Research-Driven Learning, Creativity-Enhanced Competency, and Science-Education Synergy: A Case Study of Machine Learning-Assisted Intelligent Handwriting Recognition System. University Chemistry, 2026, 41(1): 289-297. doi: 10.12461/PKU.DXHX202509083
19. [19]
  Wen-Bing Hu . Systematic Introduction of Polymer Chain Structures. University Chemistry, 2025, 40(4): 15-19. doi: 10.3866/PKU.DXHX202401014
20. [20]
  Min Hu , Yinghuan Li , Yanhong Bai , Yanping Ren , Juanjuan Song , Yongxian Fan , Dongcheng Liu , Xiuqiong Zeng , Faqiong Zhao , Wenwei Zhang , Mei Shi , Wan Li , Xiuyun Wang , Weihong Li , Xiaohang Qiu , Yong Fan , Jianrong Zhang , Shuyong Zhang . Suggestions on the Method of Hydrothermal-Solventthermal Synthesis and Their Operation Standards. University Chemistry, 2026, 41(3): 208-215. doi: 10.12461/PKU.DXHX202507034

Get Citation

PDF

XML

Metrics

PDF Downloads(796)
Abstract views(2611)
HTML views(43)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142