Citation: Hao Gu, Rui Li, Qiuying Li, Sheng Lu, Yahui Chen, Xiaoning Yang, Huili Ma, Zhijun Xu, Xiaoqiang Chen. Multi-dimensional hydrogen bonds regulated emissions of single-molecule system enabling surficial hydrophobicity/hydrophilicity mapping[J]. Chinese Chemical Letters, ;2025, 36(5): 110116. doi: 10.1016/j.cclet.2024.110116 shu

Multi-dimensional hydrogen bonds regulated emissions of single-molecule system enabling surficial hydrophobicity/hydrophilicity mapping

Hao Gu ^a ,
Rui Li ^a ,
Qiuying Li ^b ,
Sheng Lu ^{a, *,} ,
Yahui Chen ^a ,
Xiaoning Yang ^a ,
Huili Ma ^b ,
Zhijun Xu ^{a, *,} ,
Xiaoqiang Chen ^{a, *,}

a.
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, China
b.
State Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Nanjing Tech University (NanjingTech), Nanjing 211816, China

shenglu@njtech.edu.cn

xuzhijun@njtech.edu.cn

chenxq@njtech.edu.cn

Received Date: 20 March 2024
Revised Date: 16 May 2024
Accepted Date: 12 June 2024
Available Online: 13 June 2024

Figures(5)

Constructing multi-dimensional hydrogen bond (H-bond) regulated single-molecule systems with multi-emission remains a challenge. Herein, we report the design of a new excited-state intramolecular proton transfer (ESIPT) featured chromophore (HBT-DPI) that shows flexible emission tunability via the multi-dimensional regulation of intra- and intermolecular H-bonds. The feature of switchable intramolecular H-bonds is induced via incorporating several hydrogen bond acceptors and donors into one single HBT-DPI molecule, allowing the "turn on/off" of ESIPT process by forming isomers with distinct intramolecular H-bonds configurations. In response to different external H-bonding environments, the obtained four types of crystal/cocrystals vary in the contents of isomers and the molecular packing modes, which are mainly guided by the intermolecular H-bonds, exhibiting non-emissive features or emissions ranging from green to orange. Utilizing the feature of intermolecular H-bond guided molecular packing, we demonstrate the utility of this fluorescent material for visualizing hydrophobic/hydrophilic areas on large-scale heterogeneous surfaces of modified poly(1,1-difluoroethylene) (PVDF) membranes and quantitatively estimating the surface hydrophobicity, providing a new approach for hydrophobicity/hydrophilicity monitoring and measurement. Overall, this study represents a new design strategy for constructing multi-dimensional hydrogen bond regulated ESIPT-based fluorescent materials that enable multiple emissions and unique applications.
- Multi-dimensional hydrogen bonds,
- Emission regulation,
- Hydrophobicity/hydrophilicity,
- Surficial mapping,
- Excited-state intramolecular proton transfer
1. [1]
  X. Song, Y. Wang, C. Wang, et al., J. Am. Chem. Soc. 144 (2022) 10663–10687. doi: 10.1021/jacs.2c02598
2. [2]
  A.Y. Chan, I.B. Perry, N.B. Bissonnette, et al., Chem. Rev. 122 (2022) 1485–1542. doi: 10.1021/acs.chemrev.1c00383
3. [3]
  Y.H. Wang, S. Zheng, W.M. Yang, et al., Nature 600 (2021) 81–85. doi: 10.1038/s41586-021-04068-z
4. [4]
  X. Zhang, Y. Cheng, J. You, et al., Nat. Commun. 13 (2022) 1117. doi: 10.1038/s41467-022-28759-x
5. [5]
  Z. Wang, Y. Zhang, C. Wang, et al., Adv. Mater. 32 (2020) 1907355. doi: 10.1002/adma.201907355
6. [6]
  D. Li, Y. Yang, J. Yang, et al., Nat. Commun. 13 (2022) 347. doi: 10.1038/s41467-022-28011-6
7. [7]
  B.C. Gibb, Nat. Chem. 12 (2020) 665–667. doi: 10.1038/s41557-020-0524-2
8. [8]
  Z. Song, D. Mao, S.H.P. Sung, et al., Adv. Mater. 28 (2016) 7249–7256. doi: 10.1002/adma.201601214
9. [9]
  H. Park, D. Lee, Chem. Sci. 12 (2021) 590–598. doi: 10.1039/d0sc05067a
10. [10]
  Z.Y. Liu, J.W. Hu, C.H. Huang, et al., J. Am. Chem. Soc. 141 (2019) 9885–9894. doi: 10.1021/jacs.9b02765
11. [11]
  Y. Han, T. Zhang, X. Chen, et al., ACS Appl. Mater. Interfaces 13 (2021) 32270–32277. doi: 10.1021/acsami.1c08316
12. [12]
  A. Shukla, V.T.N. Mai, V.V. Divya, et al., J. Am. Chem. Soc. 144 (2022) 13499–13510. doi: 10.1021/jacs.2c02163
13. [13]
  K. Wu, T. Zhang, Z. Wang, et al., J. Am. Chem. Soc. 140 (2018) 8877–8886. doi: 10.1021/jacs.8b04795
14. [14]
  L. Gu, H. Shi, C. Miao, et al., J. Mater. Chem. C 6 (2018) 226–233. doi: 10.1039/c7tc04452f
15. [15]
  J. Chen, T. Yu, E. Ubba, et al., Adv. Opt. Mater. 7 (2019) 1801593. doi: 10.1002/adom.201801593
16. [16]
  X. Qiu, Y. Xu, C. Wang, et al., J. Mater. Chem. C 7 (2019) 5461–5467. doi: 10.1039/c9tc00357f
17. [17]
  G.R. Desiraju, T. Steiner, The Weak Hydrogen bond: in Structural Chemistry and Biology, Oxford University Press, NewYork, 2001.
18. [18]
  M. Mieczkowski, C. Steinmetzger, I. Bessi, et al., Nat. Commun. 12 (2021) 3549–3559. doi: 10.1038/s41467-021-23932-0
19. [19]
  A. Wang, R. Fan, Y. Dong, et al., ACS Appl. Mater. Interfaces 9 (2017) 15744–15757. doi: 10.1021/acsami.7b01254
20. [20]
  Y. Zhang, H. Yang, H. Ma, et al., Angew. Chem. Int. Ed. 58 (2019) 8773–8778. doi: 10.1002/anie.201902890
21. [21]
  K. Liu, G. Wang, N. Ding, et al., ACS Appl. Mater. Interfaces 13 (2021) 19342–19350. doi: 10.1021/acsami.1c03331
22. [22]
  K. Nagura, S. Saito, H. Yusa, et al., J. Am. Chem. Soc. 135 (2013) 10322–10325. doi: 10.1021/ja4055228
23. [23]
  G. Huang, Y. Jiang, J. Wang, et al., J. Mater. Chem. C 7 (2019) 12709–12716. doi: 10.1039/c9tc04501e
24. [24]
  J. Herbich, C.Y. Hung, R.P. Thummel, J. Waluk, J. Am. Chem. Soc. 118 (1996) 3508–3518. doi: 10.1021/ja952797d
25. [25]
  M. Das, S. Sahu, G. Krishnamoorthy, Phys. Chem. Chem. Phys. 21 (2019) 15669–15677. doi: 10.1039/c9cp02281c
26. [26]
  A.C. Sedgwick, L. Wu, H.H. Han, et al., Chem. Soc. Rev. 47 (2018) 8842–8880. doi: 10.1039/c8cs00185e
27. [27]
  Y. Chen, Y. Fang, H. Gu, et al., ACS Appl. Mater. Interfaces 12 (2020) 55094–55106. doi: 10.1021/acsami.0c16585
28. [28]
  C.H. Wang, Z.Y. Liu, C.H. Huang, et al., J. Am. Chem. Soc. 143 (2021) 12715–12724. doi: 10.1021/jacs.1c05602
29. [29]
  H. Gu, W. Wang, W. Wu, et al., Chem. Commun. 59 (2023) 2056–2071. doi: 10.1039/d2cc06556h
30. [30]
  K. Wang, L. Wan, J. Wang, et al., Chin. Chem. Lett. 35 (2024) 109554. doi: 10.1016/j.cclet.2024.109554
31. [31]
  Y. Chen, Y.R. Lee, W. Wang, et al., Angew. Chem. Int. Ed. 62 (2023) e202301765. doi: 10.1002/anie.202301765
32. [32]
  Q. Huang, Q. Guo, J. Lan, et al., Mater. Horiz. 8 (2021) 1499–1508. doi: 10.1039/d0mh02032j
33. [33]
  X.M. Cai, Y. Lin, Y. Li, et al., Nat. Commun. 12 (2021) 1773–1781. doi: 10.1038/s41467-021-22061-y
34. [34]
  Y. Sun, Y. Jiang, J. Jiang, T. Li, M. Liu, Chin. Chem. Lett. 35 (2024) 108409. doi: 10.1016/j.cclet.2023.108409
35. [35]
  H. Hu, X. Cheng, Z. Ma, R.P. Sijbesma, Z. Ma, J. Am. Chem. Soc. 144 (2022) 9971–9979. doi: 10.1021/jacs.2c03056
36. [36]
  K.I. Sakai, S. Tsuchiya, T. Kikuchi, T. Akutagawa, J. Mater. Chem. C 4 (2016) 2011–2016. doi: 10.1039/C5TC04290A
37. [37]
  F. Zhou, P. Gu, Z. Luo, et al., Nat. Commun. 12 (2021) 2339. doi: 10.1038/s41467-021-22685-0
38. [38]
  Y. Chen, Y. Xie, Z. Li, J. Phys. Chem. Lett. 13 (2022) 1652–1659. doi: 10.1021/acs.jpclett.2c00118
39. [39]
  B. Tang, B. Liu, H. Liu, H. Zhang, Adv. Funct. Mater. 30 (2020) 2004116. doi: 10.1002/adfm.202004116
40. [40]
  L. Han, M. Wang, L.O. Prieto-Lopez, X. Deng, J. Cui, Adv. Funct. Mater. 30 (2020) 1907064. doi: 10.1002/adfm.201907064
41. [41]
  K.W. Millsap, G. Reid, H.C. vanderMei, H.J. Busscher, Biomaterials 18 (1997) 87–91. doi: 10.1016/S0142-9612(96)00105-6
42. [42]
  L. Zhang, B. Tang, J. Wu, R. Li, P. Wang, Adv. Mater. 27 (2015) 4889–4894. doi: 10.1002/adma.201502362
43. [43]
  G. Huang, Q. Yang, Q. Xu, S.H. Yu, H.L. Jiang, Angew. Chem. Int. Ed. 55 (2016) 7379–7383. doi: 10.1002/anie.201600497
44. [44]
  A.M. Abdul-Fattah, R. Oeschger, H. Roehl, et al., Eur. J. Pharm. Biopharm. 85 (2013) 314–326. doi: 10.1016/j.ejpb.2013.06.007
45. [45]
  X. Zhang, C. Liu, J. Yang, X.J. Huang, Z.K. Xu, J. Membr. Sci. 624 (2021) 118976. doi: 10.1016/j.memsci.2020.118976
46. [46]
  X. Cheng, Y. Ye, Z. Li, et al., ACS Nano 16 (2022) 4684–4692. doi: 10.1021/acsnano.1c11388
47. [47]
  Y. Peng, L. Wang, Q. Luo, et al., Chem 4 (2018) 613–625. doi: 10.1016/j.chempr.2018.01.019
48. [48]
  S. Zhang, F. Ye, X. Wang, et al., Science 380 (2023) 404–409. doi: 10.1126/science.adg3755
49. [49]
  R. Alcalde, A. Gutierrez, M. Atilhan, S. Aparicio, J. Mol. Liq. 290 (2019) 110916. doi: 10.1016/j.molliq.2019.110916
50. [50]
  F.O. Farias, J.F.B. Pereira, J.A.P. Coutinho, L. Igarashi-Mafra, M.R. Mafra, Fluid Phase Equilib. 503 (2020) 112319. doi: 10.1016/j.fluid.2019.112319
51. [51]
  Y. Yin, C. Wu, G. Yu, et al., J. Mater. Chem. A 9 (2021) 7881–7887. doi: 10.1039/d1ta00289a
52. [52]
  Q. Xing, W. Pei, R. Xu, J. Pei, Basic Organic Chemistry (Ⅱ), Peking University Press, Beijing, 2005.
53. [53]
  S. Kabir, A.M. Sapse, J. Comput. Chem. 12 (1991) 1142–1146. doi: 10.1002/jcc.540120913
54. [54]
  D. Wang, Q. Sun, M.J. Hokkanen, et al., Nature 582 (2020) 55–59. doi: 10.1038/s41586-020-2331-8
55. [55]
  J. Zou, J. Wu, Y. Wang, et al., Chem. Soc. Rev. 51 (2022) 2972–2990. doi: 10.1039/d0cs01487g
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