Citation: LIU Pingying, LIU Chunyan, LIU Qian, MA Jing. Influence of Photoisomerization on Binding Energy and Conformation of Azobenzene-Containing Host-Guest Complex[J]. Acta Physico-Chimica Sinica, ;2018, 34(10): 1171-1178. doi: 10.3866/PKU.WHXB201803024 shu

Influence of Photoisomerization on Binding Energy and Conformation of Azobenzene-Containing Host-Guest Complex

LIU Pingying ^1,2 ,
LIU Chunyan ² ,
LIU Qian ² ,
MA Jing ^2,,

1.
School of Materials Science and Engineering, Jingdezhen Ceramic Institute, Jingdezhen 333403, Jiangxi Province, P. R. China
2.
School of Chemistry and Chemical Engineering, Key Laboratory of Mesoscopic Chemistry of MOE, Nanjing University, Nanjing 210023, P. R. China

Corresponding author: MA Jing, majing@nju.edu.cn
Received Date: 25 December 2017
Revised Date: 28 February 2018
Accepted Date: 28 February 2018
Available Online: 2 October 2018
Fund Project: The project was supported by the National Natural Science Foundation of China (21673111, 21661017) and Natural Science Foundation of Jiangxi Province, China (20161BAB203081)the National Natural Science Foundation of China 21673111the National Natural Science Foundation of China 21661017Natural Science Foundation of Jiangxi Province, China 20161BAB203081

The construction of a photo-controllable artificial molecular machine capable of realizing the light-driven motion on a molecular scale and of performing a specific function is a fascinating topic in supramolecular chemistry. The bistable switchable molecule, azobenzene (AZO), has been introduced into the supramolecular architecture as a key building block, owing to its efficient and reversible trans (E)-cis (Z) photoisomerization. The binding strength of the dibenzo[24]crown-8 (DB24C8) host and dialkylammonium-based rod-like guest consisting of an AZO moiety and the Z\begin{document}$\to $\end{document}E photoisomerization process in an interlocked host-guest complex have been investigated by the density functional theory (DFT) calculations and the reactive molecular dynamics (RMD) simulations by considering both torsion and inversion paths. The strong host-guest binding strength provides a necessary premise to stabilize the complex during the E-Z photoisomerization of the AZO unit, which is a terminal stopper to control the directional motion of the guest. A stronger binding strength for the Z isomer can be induced by the stronger hydrogen-bonding interaction. The steric effect is introduced into the Z isomer to force the ring slipping exclusively over the cyclopentyl terminal (pseudostopper). The host-guest complexation has a slight effect on the conformation of the AZO functional subunit for the two isomers. The faster Z\begin{document}$\to $\end{document}E photoisomerization process within the picosecond timescale is kinetically more favored than the dethreading of the ring through the pseudostopper subunit of the rod. After isomerization, a structure relaxation is observed for the crown ether ring within 500 ps. The flexible backbone of the crown ether ring is helpful in realizing steady and stable host-guest recognition during photoisomerization. Moreover, the orthogonality of the site-specific binding interaction is revealed by the similar binding energies obtained at similar hydrogen bonding recognition sites for various interlocked host-guest supramolecular systems although the constituents of the guests are different from each other. The introduction of two stereoisomers of the AZO subunit has little influence on the other conformations of guest subunits. These results are useful for the rational design of more sophisticated stimuli-controlled artificial molecular machines.
- Photoisomerization,
- Reactive molecular dynamics model,
- Azobenzene,
- Nanomotors,
- Pseudorotaxane,
- Supramolecular chemistry
1. [1]
  Ma, X.; Zhao, Y. Chem. Rev. 2015, 115, 7794. doi: 10.1021/cr500392w doi: 10.1021/cr500392w
2. [2]
  Szymański, W.; Beierle, J.; Kistemaker, H.; Velema, W.; Feringa, B. Chem. Rev. 2013, 113, 6114. doi: 10.1021/cr300179f doi: 10.1021/cr300179f
3. [3]
  Balzani, V.; Credi, A.; Silvi, S.; Venturi, M. Chem. Soc. Rev. 2006, 35, 1135. doi: 10.1039/b517102b doi: 10.1039/b517102b
4. [4]
  Balzani, V.; Credi, A.; Venturi, M. Chem. Soc. Rev. 2009, 38, 1542. doi: 10.1039/b806328c doi: 10.1039/b806328c
5. [5]
  Crowley, J.; Goldup, S.; Lee, A.; Leigh, D.; McBurney, R. Chem. Soc. Rev. 2009, 38, 1530. doi: 10.1039/b804243h doi: 10.1039/b804243h
6. [6]
  Erbas-Cakmak, S.; Leigh, D.; McTernan, C.; Nussbaumer, A. Chem. Rev. 2015, 115, 10081. doi: 10.1021/acs.chemrev.5b00146 doi: 10.1021/acs.chemrev.5b00146
7. [7]
  Klajn, R.; Stoddart, J.; Grzybowski, B. Chem. Soc. Rev. 2010, 39, 2203. doi: 10.1039/b920377j doi: 10.1039/b920377j
8. [8]
  Saha, S.; Stoddart, J. Chem. Soc. Rev. 2007, 36, 77. doi: 10.1039/b607187b doi: 10.1039/b607187b
9. [9]
  Tian, H.; Wang, Q. Chem. Soc. Rev. 2006, 35, 361. doi: 10.1039/b512178g doi: 10.1039/b512178g
10. [10]
  van Dongen, S.; Cantekin, S.; Elemans, J.; Rowan, A.; Nolte, R. Chem. Soc. Rev. 2014, 43, 99. doi: 10.1039/c3cs60178a doi: 10.1039/c3cs60178a
11. [11]
  Zhang, T.; Mu, L.; She, G.; Shi, W. Chem. Commun. 2012, 48, 452. doi: 10.1039/c1cc16339f doi: 10.1039/c1cc16339f
12. [12]
  Burkhart, C.; Haberhauer, G. Eur. J. Org. Chem. 2017, 2017, 1308. doi: 10.1002/ejoc.201601371 doi: 10.1002/ejoc.201601371
13. [13]
  Dey, K.; Sen, A. J. Am. Chem. Soc. 2017, 139, 7666. doi: 10.1021/jacs.7b02347 doi: 10.1021/jacs.7b02347
14. [14]
  Kathan, M.; Hecht, S. Chem. Soc. Rev. 2017, 46, 5536. doi: 10.1039/c7cs00112f doi: 10.1039/c7cs00112f
15. [15]
  Oruganti, B.; Wang, J.; Durbeej, B. Int. J. Quantum Chem. 2017, e25405. doi: 10.1002/qua.25405 doi: 10.1002/qua.25405
16. [16]
  Qu, D.; Wang, Q.; Zhang, Q.; Ma, X.; Tian, H. Chem. Rev. 2015, 115, 7543. doi: 10.1021/cr5006342 doi: 10.1021/cr5006342
17. [17]
  Baroncini, M.; Bergamini, G. Chem. Rec. 2017, 17, 700. doi: 10.1002/tcr.201600112 doi: 10.1002/tcr.201600112
18. [18]
  Ueno, A.; Yoshimura, H.; Saka, R.; Osa, T. J. Am. Chem. Soc. 1979, 101, 2779. doi: 10.1002/adom.201600281 doi: 10.1002/adom.201600281
19. [19]
  Yao, X.; Li, T.; Wang, J.; Ma, X.; Tian, H. Adv. Opt. Mater. 2016, 4, 1322. doi: 10.1002/adom.201600281 doi: 10.1002/adom.201600281
20. [20]
  Baroncini, M.; Silvi, S.; Venturi, M.; Credi, A. Angew. Chem. Int. Ed. 2012, 51, 4223. doi: 10.1002/anie.201200555 doi: 10.1002/anie.201200555
21. [21]
  Ragazzon, G.; Baroncini, M.; Silvi, S.; Venturi, M.; Credi, A. Nat. Nanotechnol. 2015, 10, 70. doi: 10.1038/nnano.2014.260 doi: 10.1038/nnano.2014.260
22. [22]
  Liu, Z.; Ma, J. J. Phys. Chem. A 2011, 115, 10136. doi: 10.1021/jp203570m doi: 10.1021/jp203570m
23. [23]
  Tian, Z.; Wen, J.; Ma, J. J. Chem. Phys. 2013, 139, 014706. doi: 10.1063/1.4812379 doi: 10.1063/1.4812379
24. [24]
  Wen, J.; Tian, Z.; Ma, J. J. Phys. Chem. C 2013, 117, 19934. doi: 10.1021/jp404434r doi: 10.1021/jp404434r
25. [25]
  Tian, Z.; Wen, J.; Ma, J. Mol. Simul. 2014, 41, 28. doi: 10.1080/08927022.2014.918974 doi: 10.1080/08927022.2014.918974
26. [26]
  Liu, C.; Zheng, D.; Hu, W.; Tian, Z.; Zhao, J.; Zhu, Y.; Ma, J. Nanoscale 2017, 9, 16700. doi: 10.1039/C7NR03421K doi: 10.1039/C7NR03421K
27. [27]
  Zhao, J.; Liu, C.; Ma, J. Nanoscale 2017, 9, 19017. doi: 10.1039/c7nr07382h doi: 10.1039/c7nr07382h
28. [28]
  Pang, J.; Tian, Z.; Ma, J. Sci. Sin. Chim. 2015, 45, 412. doi: 10.1360/n032014-00250 doi: 10.1360/n032014-00250
29. [29]
  Zheng, D.; Yuan, X.; Ma, J. Acta Phys. -Chim. Sin. 2016, 32, 290. doi: 10.3866/PKU.WHXB201512072
30. [30]
  Tabacchi, G.; Silvi, S.; Venturi, M.; Credi, A.; Fois, E. ChemPhysChem 2016, 17, 1913. doi: 10.1002/cphc.201501160 doi: 10.1002/cphc.201501160
31. [31]
  Bandara, H.; Burdette, S. Chem. Soc. Rev. 2012, 41, 1809. doi: 10.1039/c1cs15179g doi: 10.1039/c1cs15179g
32. [32]
  Ciminelli, C.; Granucci, G.; Persico, M. Chemistry 2004, 10, 2327. doi: 10.1002/chem.200305415 doi: 10.1002/chem.200305415
33. [33]
  Floss, G.; Saalfrank, P. J. Phys. Chem. A 2015, 119, 5026. doi: 10.1021/acs.jpca.5b02933 doi: 10.1021/acs.jpca.5b02933
34. [34]
  Gao, A.; Li, B.; Zhang, P.; Han, K. J. Chem. Phys. 2012, 137, 204305. doi:10.1063/1.4767459 doi: 10.1063/1.4767459
35. [35]
  Ishikawa, T.; Noro, T.; Shoda, T. J. Chem. Phys. 2001, 115, 7503. doi: 10.1063/1.1406975 doi: 10.1063/1.1406975
36. [36]
  Li, Y.; Hartke, B. J. Chem. Phys. 2013, 139, 224303. doi: 10.1063/1.4837237 doi: 10.1063/1.4837237
37. [37]
  Pederzoli, M.; Pittner, J.; Barbatti, M.; Lischka, H. J. Phys. Chem. A 2011, 115, 11136. doi:10.1021/jp2013094 doi: 10.1021/jp2013094
38. [38]
  Tiberio, G.; Muccioli, L.; Berardi, R.; Zannoni, C. ChemPhysChem 2010, 11, 1018. doi: 10.1002/cphc.200900652 doi: 10.1002/cphc.200900652
39. [39]
  Yin, T.; Zhao, Z.; Zhang, H. RSC Adv. 2016, 6, 79879. doi: 10.1039/c6ra10880f doi: 10.1039/c6ra10880f
40. [40]
  Bockmann, M.; Braun, S.; Doltsinis, N.; Marx, D. J. Chem. Phys. 2013, 139, 084108. doi: 10.1063/1.4818489 doi: 10.1063/1.4818489
41. [41]
  Liu, P.; Chen, Q.; Ma, J. J. Comput. Chem. 2016, 37, 2228. doi: 10.1002/jcc.24452 doi: 10.1002/jcc.24452
42. [42]
  Liu, P.; Chen, Q.; Ma, J. Sci. Sin. Chim. 2016, 46, 69. doi: 10.1360/N032015-00152 doi: 10.1360/N032015-00152
43. [43]
  Liu, P.; Li, W.; Liu, L.; Wang, L.; Ma, J. J. Phys. Chem. A 2014, 118, 9032. doi: 10.1021/jp5020516 doi: 10.1021/jp5020516
44. [44]
  Ashton, P.; Ballardini, R.; Balzani, V.; Baxter, I.; Credi, A.; Fyfe, M.; Gandolfi, M.; Gomez-Lopez, M.; Martinez-Diaz, M.; Piersanti, A.; et al. J. Am. Chem. Soc. 1998, 120, 11932. doi:10.1021/ja982167m doi: 10.1021/ja982167m
45. [45]
  Frisch, M. ; Trucks, G. ; Schlegel, H. ; Scuseria, G. ; Robb, M. ; Cheeseman, J. ; Scalmani, G. ; Barone, V. ; Mennucci, B. ; Petersson, G. et al. Gaussian 09, Revision B. 01; Gaussian Inc. : Wallingford, CT, USA, 2010.
46. [46]
  Li, S.; Li, W.; Fang, T. J. Am. Chem. Soc. 2005, 127, 7215. doi: 10.1021/ja0427247 doi: 10.1021/ja0427247
47. [47]
  Li, W.; Li, S.; Jiang, Y. J. Phys. Chem. A 2007, 111, 2193. doi: 10.1021/jp067721q doi: 10.1021/jp067721q
48. [48]
  Li, S.; Li, W.; Ma, J. Acc. Chem. Res. 2014, 47, 2712. doi: 10.1021/ar500038z doi: 10.1021/ar500038z
49. [49]
  Boys, S.; Bernardi, F. Mol. Phys. 1970, 19, 553. doi: 10.1080/00268977000101561 doi: 10.1080/00268977000101561
50. [50]
  Simon, S.; Duran, M.; Dannenberg, J. J. Chem. Phys. 1996, 105, 11024. doi: 10.1063/1.472902 doi: 10.1063/1.472902
51. [51]
  van Duin, A.; Dasgupta, S.; Lorant, F.; Goddard, W. J. Phys. Chem. A 2001, 105, 9396. doi: 10.1021/jp004368u doi: 10.1021/jp004368u
52. [52]
  Mueller, J.; van Duin, A.; Goddard, W. J. Phys. Chem. C 2010, 114, 4939. doi: 10.1021/jp9035056 doi: 10.1021/jp9035056
53. [53]
  Brenner, D.; Shenderova, O.; Harrison, J.; Stuart, S.; Ni, B.; Sinnott, S. J. Phys.: Condens. Matter 2002, 14, 783. doi: 10.1088/0953-8984/14/4/312 doi: 10.1088/0953-8984/14/4/312
54. [54]
  Yu, J.; Sinnott, S.; Phillpot, S. Phys. Rev. B 2007, 75, 085311. doi: 10.1103/PhysRevB.75.085311 doi: 10.1103/PhysRevB.75.085311
55. [55]
  Shan, T.; Devine, B.; Hawkins, J.; Asthagiri, A.; Phillpot, S.; Sinnott, S. Phys. Rev. B 2010, 82, 235302. doi: 10.1103/PhysRevB.82.235302 doi: 10.1103/PhysRevB.82.235302
56. [56]
  Materials Studio, Version 4. 0; Accelrys, Inc. : San Diego, CA, USA, 2006.
57. [57]
  Liu, P.; Li, W.; Kan, Z.; Sun, H.; Ma, J. J. Phys. Chem. A 2016, 120, 490. doi: 10.1021/acs.jpca.5b10085 doi: 10.1021/acs.jpca.5b10085
1. [1]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
2. [2]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
3. [3]
  Zixi Zou , Jingyuan Wang , Yian Sun , Qian Wang , Da-Hui Qu . Controlling molecular assembly on time scale: Time-dependent multicolor fluorescence for information encryption. Chinese Chemical Letters, 2024, 35(7): 108972-. doi: 10.1016/j.cclet.2023.108972
4. [4]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
5. [5]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
6. [6]
  Kang Wei , Jiayu Li , Wen Zhang , Bing Yuan , Ming-De Li , Pingwu Du . A strained π-extended [10]cycloparaphenylene carbon nanoring. Chinese Chemical Letters, 2024, 35(5): 109055-. doi: 10.1016/j.cclet.2023.109055
7. [7]
  Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
8. [8]
  Ling Zhang , Jing Kang . Turn Waste into Valuable: Preparation of High-Strength Water-Based Adhesives from Polymethylmethacrylate Wastes: a Comprehensive Chemical Experiments. University Chemistry, 2024, 39(2): 221-226. doi: 10.3866/PKU.DXHX202306075
9. [9]
  Jiarui Wu , Gengxin Wu , Yan Wang , Yingwei Yang . Crystal Engineering Based on Leaning Towerarenes. University Chemistry, 2024, 39(3): 58-62. doi: 10.3866/PKU.DXHX202304014
10. [10]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
11. [11]
  Peiwen Liu , Fang Zhao , Jing Zhang , Yunpeng Bai , Jinxing Ye , Bo Bao , Xinggui Zhou , Li Zhang , Changlu Zhou , Xinhai Yu , Peng Zuo , Jianye Xia , Lian Cen , Yangyang Yang , Guoyue Shi , Lin Xu , Weiping Zhu , Yufang Xu , Xuhong Qian . Micro/nano flow chemistry by Beyond Limits Manufacturing. Chinese Chemical Letters, 2024, 35(5): 109020-. doi: 10.1016/j.cclet.2023.109020
12. [12]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
13. [13]
  Yingxiao Zong , Yangfei Wei , Xiaoqing Liu , Junke Wang , Huanfang Guo , Junli Wang , Zhuangzhi Shi , Tao Tu , Cheng Yang , Chongyang Wang , Leyong Wang . The 4^th CCL Organic Chemistry Forum held in Zhangye. Chinese Chemical Letters, 2024, 35(8): 109743-. doi: 10.1016/j.cclet.2024.109743
14. [14]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
15. [15]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
16. [16]
  Wenlong Li , Feishi Shan , Qingdong Bao , Qinghua Li , Hua Gao , Leyong Wang . Supramolecular assembly nanoparticle for trans-epithelial treatment of keratoconus. Chinese Chemical Letters, 2024, 35(10): 110060-. doi: 10.1016/j.cclet.2024.110060
17. [17]
  Guoxing Liu , Yixin Li , Changming Tian , Yongmei Xiao , Lijie Liu , Zhanqi Cao , Song Jiang , Xin Zheng , Caoyuan Niu , Yun-Lai Ren , Liangru Yang , Xianfu Zheng , Yong Chen . Highly reversible photomodulated hydrosoluble stiff-stilbene supramolecular luminophor induced by cucurbituril. Chinese Chemical Letters, 2024, 35(8): 109403-. doi: 10.1016/j.cclet.2023.109403
18. [18]
  Gang Lang , Jing Feng , Bo Feng , Junlan Hu , Zhiling Ran , Zhiting Zhou , Zhenju Jiang , Yunxiang He , Junling Guo . Supramolecular phenolic network-engineered C–CeO₂ nanofibers for simultaneous determination of isoniazid and hydrazine in biological fluids. Chinese Chemical Letters, 2024, 35(6): 109113-. doi: 10.1016/j.cclet.2023.109113
19. [19]
  Lei Zhou , Youjun Zhou , Lizhen Fang , Yiqiao Bai , Yujia Meng , Liang Li , Jie Yang , Yong Yao . Pillar[5]arene based artificial light-harvesting supramolecular polymer for efficient and recyclable photocatalytic applications. Chinese Chemical Letters, 2024, 35(9): 109509-. doi: 10.1016/j.cclet.2024.109509
20. [20]
  Xingwen Cheng , Haoran Ren , Jiangshan Luo . Boosting the self-trapped exciton emission in vacancy-ordered double perovskites via supramolecular assembly. Chinese Journal of Structural Chemistry, 2024, 43(6): 100306-100306. doi: 10.1016/j.cjsc.2024.100306

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(400)
HTML views(80)

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