English

Structure–Property Relationship of Light-Responsive Wormlike Micelles Using Methoxycinnamate Derivatives as Light-Switchable Molecules

• Liu Tongqing ^1, ,
• Xue Fangfang ^2,3, ,
• Yi Ping ^2,3, ,
• Xia Zhiyu ^1, ,
• Dong Jinfeng ^{1, ,} ,
• Li Xuefeng ^{1, ,}

• 1.

  Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. China

• 2.

  Oil and Gas Technology Research Institute, PetroChina Changqing Oilfield Company, Xi'an 710018, P. R. China

• 3.

  National Engineering Laboratory for Exploration and Development of Low Permeability Oil and Gas Fields, Xi'an 710018, P. R. China

Corresponding author: Dong Jinfeng, jfdong@whu.edu.cn Li Xuefeng, lixuefeng@whu.edu.cn

• Received Date: 07 October 2019
  Accepted Date: 07 November 2019
  Revised Date: 01 November 2019
  Available Online: 15 October 2020
• Fund Project:

  The project was supported by the National Natural Science Foundation of China (21573164, 21773174)

Abstract: In this work, light-responsive viscoelastic wormlike micelles based on cetyltrimethylammonium hydroxide (CTAOH) and cinnamic acid derivatives, including cinnamic acid (CA), 2-methoxycinnamic acid (2-MCA), 3-methoxycinnamic acid (3-MCA), 4-methoxycinnamic acid (4-MCA), 2, 3-dimethoxycinnamic acid (2, 3-DMCA), 2, 4-dimethoxycinnamic acid (2, 4-DMCA), 2, 3, 4-trimethoxycinnamic acid (2, 3, 4-DMCA), and 3, 4, 5-trimethoxycinnamic acid (3, 4, 5-DMCA), were prepared. The effects of the CA derivative structures, especially the position and number of methoxy moieties, on the formation of wormlike micelles were systematically determined. The CA derivatives facilitated the formation of long and entangled wormlike micelles. ¹H NMR results showed that the CA derivatives participated in the formation of wormlike micelles via insertion of the aromatic moieties into the aggregates. The number of methoxy moieties had a much stronger effect on the viscosity of the wormlike micelle solution than the position of this moiety. The larger the number of methoxy moiety, the smaller was the aggregate. Substituted methoxy moieties increased the steric hindrance between the surfactants and CA molecules, thus hindering the formation of large aggregates. However, the position of the methoxy moiety had a predominant effect on the UV-light-induced transition of the wormlike micelles. Specifically, the ortho-methoxy moiety in the CA molecules dramatically enhanced the efficiency of UV-light-induced trans-cis isomerization. For example, the 2-MCA/CTAOH, 3-MCA/CTAOH, and 4-MCA/CTAOH binary systems (90 mmol·L^-1/100 mmol·L^-1) were gel-like with similar viscosities of around 20 Pa·s, but after UV light irradiation, they were transformed into a fluid with lower viscosity because of the formation of smaller aggregates. However, the irradiation time required for the transition varied significantly, as suggested by the results of viscosity measurements and UV-Vis spectroscopy. The 2-MCA/CTAOH system underwent complete phase transition within 3 h, whereas continuous transitions were observed for the 3-MCA/CTAOH and 4-MCA/CTAOH systems upon irradiation for 24 h. ¹H NMR results suggested that the change in the configuration of MCA in the micelles before and after irradiation was the major cause of the abovementioned difference in the phase transition pattern. Initially, all the aromatic moieties of the trans-2-MCA molecules were deeply inserted into the hydrophobic cores of the micelles in a vertical manner, and the ionized carboxyl moiety was located in the palisade layer because of the electrostatic interactions between CTAOH and trans-2-MCA. In contrast, cis-2-MCA was inserted into the micelles in a horizontal manner, and some of the protons in the aromatic moiety were also transferred from the micellar core to the polar palisade layer. Accordingly, the CTAOH and cis-2-MCA molecules were packed loosely in the aggregates, thereby resulting in the formation of spherical micelles. Similar UV-light-induced transitions were observed for the 3-MCA/CTAOH and 4-MCA/CTAOH systems.

Key words:
• Cetyltrimethylammonium hydroxide
•  /  Cinnamic acid derivative
•  /  Wormlike micelle
•  /  Light response
•  /  trans-cis isomerization

• 1. [1]

     Mai, Y.; Eisenberg, A. Chem. Soc. Rev. 2012, 41, 5969. doi: 10.1039/c2cs35115c

  2. [2]

     Holder, S. J.; Sommerdijk, N. A. J. M. Polym. Chem. 2011, 2, 1018. doi: 10.1039/c0py00379d

  3. [3]

     Song, S. S.; Song, A. X.; Hao, J. C. RSC Adv. 2014, 4, 41864. doi: 10.1039/c4ra04849k

  4. [4]

     Webber, M. J.; Langer, R. Chem. Soc. Rev. 2017, 46, 6600. doi: 10.1039/c7cs00391a

  5. [5]

     Schramm, L. L.; Stasiuk, E. N.; Marangoni, D. G. Annu. Rep. Sect. C (Phys. Chem.) 2003, 99, 3. doi: 10.1039/b208499f

  6. [6]

     Sachse, A.; Garcia-Martinez, J. Chem. Mater. 2017, 29, 3827. doi: 10.1021/acs.chemmater.7b00599

  7. [7]

     龚铃堰, 廖广志, 陈权生, 栾和鑫, 冯玉军.物理化学学报, 2019, 35, 816. doi: 10.3866/PKU.WHXB201810060Gong, L. Y.; Liao, G. Z.; Chen, Q. S.; Luan, H. X.; Feng, Y. J. Acta Phys. -Chim. Sin. 2019, 35, 816. doi: 10.3866/PKU.WHXB201810060

  8. [8]

     Zarzar, L. D.; Sresht, V.; Sletten, E. M.; Kalow, J. A.; Blankschtein, D.; Swager, T. M. Nature 2015, 518, 520. doi: 10.1038/nature14168

  9. [9]

     Brown, P.; Butts, C. P.; Eastoe, J. Soft Matter 2013, 9, 2365. doi: 10.1039/c3sm27716j

  10. [10]

      Hu, X.; Zhang, Y. Q.; Xie, Z. G.; Jing, X. B.; Bellotti, A.; Gu, Z. Biomacromolecules 2017, 18, 649. doi: 10.1021/acs.biomac.6b01704

  11. [11]

      王喆, 贾康乐, 刘同庆, 胡俊文, 李学丰, 董金凤.物理化学学报, 2019, 35, 84. doi: 10.3866/PKU.WHXB201712251Wang, Z.; Jia, K. L.; Liu, T. Q.; Hu, J. W.; Li, X. F.; Dong, J. F. Acta Phys. -Chim. Sin. 2019, 35, 84. doi: 10.3866/PKU.WHXB201712251

  12. [12]

      Zhang, W. B.; Gao, C. Y. J. Mater. Chem. A 2017, 5, 16059. doi: 10.1039/c7ta02038d

  13. [13]

      Li, L.; Yang, Y.; Dong, J. F.; Li, X. F. J. Colloid Interface Sci. 2010, 343, 504. doi: 10.1016/j.jcis.2009.11.056

  14. [14]

      Wang, D.; Dong, R. H.; Long, P. F.; Hao, J. C. Soft Matter 2011, 7, 10713. doi: 10.1039/c1sm05949a

  15. [15]

      Lin, Y. Y.; Cheng, X. H.; Qiao, Y.; Yu, C. L.; Li, Z. B.; Yan, Y.; Huang, J. B. Soft Matter 2010, 6, 902. doi: 10.1039/b916721h

  16. [16]

      Xia, Z. Y.; Jia, K. L.; Li, X. F.; Dong, J. F. RSC Adv. 2016, 6, 45673. doi: 10.1039/c6ra05529j

  17. [17]

      Faure, D.; Gravier, J.; Labrot, T.; Desbat, B.; Oda, R.; Bassani, D. M. Chem. Commun. 2005, 1167. doi: 10.1039/b416287k

  18. [18]

      Song B. L.; Hu, Y. F.; Zhao, J. X. J. Colloid Interface Sci. 2009, 333, 820. doi: 10.1016/j.jcis.2009.02.030

  19. [19]

      Lu, Y. C.; Zhou, T. F.; Fan, Q.; Dong, J. F.; Li, X. F. J. Colloid Interface Sci. 2013, 412, 107. doi: 10.1016/j.jcis.2013.09.014

  20. [20]

      Li, J.; Zhao, M. W.; Zhou, H. T.; Gao, H. J.; Zheng, L. Q. Soft Matter 2012, 8, 7858. doi: 10.1039/c2sm25218j

  21. [21]

      Jiang, H. J.; Jiang, Y. Q.; Han, J. L.; Zhang, L.; Liu, M. H. Angew. Chem. Int. Ed. 2019, 58, 785. doi: 10.1002/anie.201811060

  22. [22]

      Davies, T. S.; Ketner, A. M.; Raghavan, S. R. J. Am. Chem. Soc. 2006, 128, 6669. doi: 10.1021/ja060021e

  23. [23]

      Tu, Y.; Gao, M. G.; Teng, H. N.; Shang, Y. Z.; Fang, B.; Liu, H. L. RSC Adv. 2018, 8, 16004. doi: 10.1039/c8ra01070f

  24. [24]

      Jiang, H. J.; Jiang, Y. Q.; Zhang, L.; Guo, Z. X.; Liu, M. H. J. Phys. Chem. C 2018, 122, 12559. doi: 10.1021/acs.jpcc.8b03412

  25. [25]

      Jia, K. L.; Hu, J. W.; Dong, J. F.; Li, X. F. J. Colloid Interface Sci. 2016, 477, 156. doi: 10.1016/j.jcis.2016.05.046

  26. [26]

      Kumar, R.; Ketner, A. M.; Raghavan, S. R. Langmuir 2010, 26, 5405. doi: 10.1021/la903834q

  27. [27]

      Feitosa, E.; Brazolin, M. R. S.; Naal, R. M. Z. G.; de Morais Del, M. P. F.; Lopes, J. R.; Loh, W.; Vasilescu, M. J. Colloid Interface Sci. 2006, 299, 883. doi: 10.1016/j.jcis.2006.02.051

  28. [28]

      Liu, C. C.; Cui, J. W.; Song, A. X.; Hao, J. C. Soft Matter 2011, 7, 8952. doi: 10.1039/c1sm05635b

  29. [29]

      Dreiss, C. A. Soft Matter. 2007, 3, 956. doi: 10.1039/b705775j

  30. [30]

      Candau, S. J.; Oda, R. Colloids Surf. A: Physicochem. Eng. Asp. 2001, 183, 5. doi: 10.1016/S0927-7757(01)00535-0

  31. [31]

      Candau, S. J.; Khatory, A.; Lequeux, F.; Kern, F. J. Phys. IV 1993, 3, 197. doi: 10.1051/jp4:1993117

  32. [32]

      Moitzi, C.; Freiberger, N.; Glatter, O. J. Phys. Chem. B 2005, 109, 16161. doi: 10.1021/jp0441691

  33. [33]

      Oh, H.; Ketner, A. M.; Heymann, R.; Kesselman, E.; Danino, D.; Falvey, D. E.; Raghavan, S. R. Soft Matter 2013, 9, 5025. doi: 10.1039/c3sm00070b

  34. [34]

      Yang, Y.; Dong, J. F.; Li, X. F. J. Disper. Sci. Technol. 2013, 34, 47. doi: 10.1080/01932691.2011.646616

  35. [35]

      Han, Y. X.; Wei, Y. Q.; Wang, H.; Mei, Y. J.; Zhou, H. J. Surfact. Deterg. 2013, 16, 139. doi: 10.1007/s11743-012-1364-x

  36. [36]

      Bachofer, S. J.; Simonis, U.; Nowicki, T. A. J. Phys. Chem. 1991, 95, 480. doi: 10.1021/j100154a084

  37. [37]

      Ketner, A. M.; Kumar, R.; Davies, T. S.; Elder, P. W.; Raghavan, S. R. J. Am. Chem. Soc. 2007, 129, 1553. doi: 10.1021/ja065053g

  38. [38]

      Tu, Y.; Chen, Q. H.; Shang, Y. H.; Teng, H. N.; Liu, H. L. Langmuir 2019, 35, 4634. doi: 10.1021/acs.langmuir.8b04290

  39. [39]

      Sakai, H.; Taki, S.; Tsuchiya, K.; Matsumura, A.; Sakai, K.; Abel, M. Chem. Lett. 2012, 41, 247. doi: 10.1246/cl.2012.247

  40. [40]

      Miyazaki, Y.; Yamamoto, K.; Aoki, J.; Ikeda, T.; Inokuchi, Y.; Ehara, M.; Ebata, T. J. Chem. Phys. 2014, 141, 244313. doi: 10.1063/1.4904268

  41. [41]

      Song, S.; Han, Y.; Hao, W.; Lu, J.; Qian Y. Tenside Surf. Det. 2017, 54, 45. doi: 10.3139/113.110479

•