Citation: Xuan Zhao, Long Zhao, Qiuyun Xiao, Hai Xiong. Intermolecular hydrogen-bond interaction to promote thermoreversible 2'-deoxyuridine-based AIE-organogels[J]. Chinese Chemical Letters, ;2021, 32(4): 1363-1366. doi: 10.1016/j.cclet.2020.10.008 shu

Intermolecular hydrogen-bond interaction to promote thermoreversible 2'-deoxyuridine-based AIE-organogels

Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China

hai.xiong@szu.edu.cn

Received Date: 30 August 2020
Revised Date: 22 September 2020
Accepted Date: 10 October 2020
Available Online: 12 October 2020

Figures(5)

Fluorescent supramolecular nucleoside-based organogels or hydrogels have attracted increasing attention owing to their tunable stability, drug delivery, tissue engineering, and inherent biocompatibility for applications in designing sensors. As the temperature of a constant TPE-Octa-dU gelator at MGC as low as 0.2 wt% was increased with gel to sol transition, a progressive decrease in the fluorescence intensity was observed. ¹H NMR study in ethanol-d₆/H₂O revealed the existence of intermolecular hydrogen-bond interaction between uridine nucleobase and triazole moieties. Based on these experiments, thus organogels induced by hydrogen bonding can promote an aggregation-induced emission (AIE) of TPE moiety. Thermoreversible gelation properties have been investigated systematically, including AIE-shapemorphing architecture owing to their unique solid-liquid interface and easy processability. At the same line, the related TPE-EdU derivative which was synthesized from 5-ethynyl-2'-deoxyuridine does not deliver organogels or hydrogels, and under similar circumstances TPE moiety of TPE-EdU does not efficiently exhibit AIE phenomenon either.
- Supramolecular,
- Organogel,
- Aggregation-induced emission,
- Nucleoside,
- Click chemistry
1. [1]
  A.S. Hoffman, Adv. Drug Deliv. Rev. 54(2002) 3-12. doi: 10.1016/S0169-409X(01)00239-3
2. [2]
  H.T. West, C.M. Csizmar, C.R. Wagner, Biomacromolecules 19(2018) 2650-2656. doi: 10.1021/acs.biomac.8b00254
3. [3]
  X. Liu, Q. Zhang, G.H. Gao, Adv. Funct. Mater. 27(2017) 170312-170317.
4. [4]
  Y.J. Yun, S.M. Park, B.H. Kim, Chem. Commun. (2003) 254-255.
5. [5]
  K. Sugiyasu, M. Numata, N. Fujita, et al., Chem. Commun. (2004) 1996-1997.
6. [6]
  F. Chen, D. Zhou, J.H. Wang, et al., Angew. Chem. Int. Ed. 57(2018) 6568-6571. doi: 10.1002/anie.201803366
7. [7]
  S. Li, S. Dong, W. Xu, et al., Adv. Sci. 5(2018) 1700527. doi: 10.1002/advs.201700527
8. [8]
  Z. Li, T.Y. Wang, F. Zhu, Z. Wang, Y.W. Li, Chin. Chem. Lett. 31(2020) 783-786. doi: 10.1016/j.cclet.2019.05.021
9. [9]
  P. Yang, S. Zhang, X.F. Chen, et al., Mater. Horiz. 7(2020) 746-761. doi: 10.1039/C9MH01197H
10. [10]
  G.M. Peters, L.P. Skala, T.N. Plank, et al., J. Am. a Chem. Soc. 137(2015) 5819-5827. doi: 10.1021/jacs.5b02753
11. [11]
  H. Zhao, D.W. Jiang, A.H. Schafer, F. Seela, ChemPlusChem 82(2017) 778-784. doi: 10.1002/cplu.201700156
12. [12]
  T. Bhattacharyya, P. Saha, J. Dash, ACS Omega 3(2018) 2230-2241. doi: 10.1021/acsomega.7b02039
13. [13]
  R. Zhong, Q. Tang, S. Wang, et al., Adv. Mater. 30(2018) e1706887. doi: 10.1002/adma.201706887
14. [14]
  K.J. Skilling, B. Kellam, M. Ashford, T.D. Bradshaw, M. Marlow, Soft Matter 12(2016) 8950-8957. doi: 10.1039/C6SM01779G
15. [15]
  F. Tang, H. Feng, Y. Du, et al., Chem. Asian J. 18(2018) 1962-1971.
16. [16]
  Q. Tang, T.N. Plank, T. Zhu, et al., ACS Appl. Mater. Interfaces 11(2019) 19743-19750. doi: 10.1021/acsami.9b02265
17. [17]
  J. Luo, Z. Xie, J.W. Lam, et al., Chem. Commun. (2001) 1740-1741.
18. [18]
  G. Feng, B. Liu, Acc. Chem. Res. 51(2018) 1404-1414. doi: 10.1021/acs.accounts.8b00060
19. [19]
  M. Kang, C. Zhou, S. Wu, et al., J. Am. Chem. Soc. 141(2019) 16781-16789. doi: 10.1021/jacs.9b07162
20. [20]
  M. Huo, Q.Q. Ye, H.L. Che, et al., Macromolecules 50(2017) 1126-1133. doi: 10.1021/acs.macromol.6b02499
21. [21]
  Y. Yang, S. Zhang, X. Zhang, et al., Nat. Commun. 10(2019) 3165-3172. doi: 10.1038/s41467-019-11144-6
22. [22]
  L.J. Chen, Y.Y. Ren, N.W. Wu, et al., J. Am. Chem. Soc. 137(2015) 11725-11735. doi: 10.1021/jacs.5b06565
23. [23]
  Y.X. Hu, X. Hao, L. Xu, et al., J. Am. Chem. Soc. 142(2020) 6285-6294. doi: 10.1021/jacs.0c00698
24. [24]
  H.T. Bui, J. Kim, H.J. Kim, B.K. Cho, S. Cho, J. Phys. Chem. C 120(2016) 26695-26702. doi: 10.1021/acs.jpcc.6b10026
25. [25]
  J.L. Zhu, X. Liu, J.H. Huang, L. Xu, Chin. Chem. Lett. 30(2019) 1767-1774. doi: 10.1016/j.cclet.2019.08.027
26. [26]
  Z. Wang, J. Nie, W. Qin, Q. Hu, B.Z. Tang, Nat. Commun. 7(2016) 12033-12040. doi: 10.1038/ncomms12033
27. [27]
  F. Seela, H. Xiong, P. Leonard, S. Budow, Org. Biomol. Chem. 7(2009) 1374-1387. doi: 10.1039/b822041g
28. [28]
  G. Qing, H. Xiong, F. Seela, T. Sun, J. Am. Chem. Soc. 132(2010) 15228-15232. doi: 10.1021/ja105246b
29. [29]
  H. Xiong, F. Seela, J. Org. Chem. 76(2011) 5584-5597. doi: 10.1021/jo2004988
30. [30]
  H. Xiong, P. Leonard, F. Seela, Bioconjug. Chem. 23(2012) 856-870. doi: 10.1021/bc300013k
31. [31]
  H. Xiong, F. Seela, Bioconjug. Chem. 23(2012) 1230-1243. doi: 10.1021/bc300074k
32. [32]
  A. Qin, J.W.Y. Lam, L. Tang, et al., Macromolecules 42(2009) 1421-1424. doi: 10.1021/ma8024706
33. [33]
  J. Liu, H. Su, L. Meng, et al., Chem. Sci. 3(2012) 2737-2747. doi: 10.1039/c2sc20382k
34. [34]
  B. He, H. Su, T. Bai, et al., J. Am. Chem. Soc. 139(2017) 5437-5443. doi: 10.1021/jacs.7b00929
35. [35]
  J.H. Jung, K. Nakashima, S. Shinkai, Nano Lett. 1(2001) 145-148. doi: 10.1021/nl000190b
36. [36]
  S. Mann, Nat. Mater. 8(2009) 781-792. doi: 10.1038/nmat2496
37. [37]
  F.M. Menger, K.L. Caran, J. Am. Chem. Soc. 122(2000) 11679-11691. doi: 10.1021/ja0016811
38. [38]
  A. Nuthanakanti, S.G. Srivatsan, Nanoscale 8(2016) 3607-3619. doi: 10.1039/C5NR07490H
39. [39]
  F. Wu, X. Wu, Z. Duan, et al., Small 15(2019) e1804839. doi: 10.1002/smll.201804839
40. [40]
  S. Rammensee, D. Huemmerich, K.D. Hermanson, T. Scheibel, A.R. Bausch, Appl. Phys. A 82(2005) 261-264.
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