Citation: Tangxin Xiao, Xiuxiu Li, Liangliang Zhang, Kai Diao, Zheng-Yi Li, Xiao-Qiang Sun, Leyong Wang. Artificial stepwise light harvesting system in water constructed by quadruple hydrogen bonding supramolecular polymeric nanoparticles[J]. Chinese Chemical Letters, ;2024, 35(2): 108618. doi: 10.1016/j.cclet.2023.108618 shu

Artificial stepwise light harvesting system in water constructed by quadruple hydrogen bonding supramolecular polymeric nanoparticles

Tangxin Xiao ^{a, *,} ,
Xiuxiu Li ^a ,
Liangliang Zhang ^a ,
Kai Diao ^{a, b} ,
Zheng-Yi Li ^a ,
Xiao-Qiang Sun ^a ,
Leyong Wang ^{b, *,}

a.
Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
b.
Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China

^☆

xiaotangxin@cczu.edu.cn

lywang@nju.edu.cn

Received Date: 11 February 2023
Revised Date: 18 May 2023
Accepted Date: 25 May 2023
Available Online: 26 May 2023

Figures(5)

Stepwise energy transfer is ubiquitous in natural photosynthesis, which greatly promotes the widespread use of solar energy. Herein, we constructed a supramolecular light harvesting system based on sequential energy transfer through the hierarchical self-assembly of M, which contains a cyanostilbene core flanked by two ureidopyrimidinone motifs, endowing itself with both aggregation-induced emission behavior and quadruple hydrogen bonding ability. The monomer M can self-assemble into hydrogen bonded polymers and then form supramolecular polymeric nanoparticles in water through a mini-emulsion process. The nanoparticles were further utilized to encapsulate the relay acceptor ESY and the final acceptor NDI to form a two-step FRET system. Tunable fluorescence including a white-light emission was successfully achieved. Our work not only shows a desirable way for the fabrication of efficient two-step light harvesting systems, but also shows great potential in tunable photoluminescent nanomaterials.
- Light harvesting system,
- Supramolecular polymer,
- Quadruple hydrogen bonding,
- AIE,
- Self-assembly
1. [1]
  M. Schulze, V. Kunz, P.D. Frischmann, et al., Nat. Chem. 8 (2016) 576–583. doi: 10.1038/nchem.2503
2. [2]
  X. Qin, M. Suga, T. Kuang, et al., Science 348 (2015) 989–995. doi: 10.1126/science.aab0214
3. [3]
  J. Otsuki, J. Mater. Chem. A 6 (2018) 6710–6753. doi: 10.1039/c7ta11274b
4. [4]
  S. Guo, Y. Song, Y. He, et al., Angew. Chem. Int. Ed. 57 (2018) 3163–3167. doi: 10.1002/anie.201800175
5. [5]
  C. Ma, N. Han, Y. Wang, et al., Chin. Chem. Lett. 34 (2023) 108081. doi: 10.1016/j.cclet.2022.108081
6. [6]
  K. Wang, K. Velmurugan, B. Li, et al., Chem. Commun. 57 (2021) 13641–13654. doi: 10.1039/d1cc06011b
7. [7]
  Y.X. Hu, W.J. Li, P.P. Jia, et al., Adv. Opt. Mater. 8 (2020) 2000265. doi: 10.1002/adom.202000265
8. [8]
  T. Xiao, W. Zhong, L. Zhou, et al., Chin. Chem. Lett. 30 (2019) 31–36. doi: 10.1016/j.cclet.2018.05.034
9. [9]
  H.Q. Peng, L.Y. Niu, Y.Z. Chen, et al., Chem. Rev. 115 (2015) 7502–7542. doi: 10.1021/cr5007057
10. [10]
  P.D. Frischmann, K. Mahata, F. Würthner, Chem. Soc. Rev. 42 (2013) 1847–1870. doi: 10.1039/C2CS35223K
11. [11]
  R. Ziessel, A. Harriman, Chem. Commun. 47 (2011) 611–631. doi: 10.1039/C0CC02687E
12. [12]
  R. Wang, M. Hao, G. Sun, et al., J. Xihua Univ. Nat. Sci. Ed. 39 (2020) 9–19.
13. [13]
  H. Qian, T. Xiao, R.B.P. Elmes, et al., Chin. Chem. Lett. 34 (2023) 108185. doi: 10.1016/j.cclet.2023.108185
14. [14]
  D. Zhang, W. Yu, S. Li, et al., J. Am. Chem. Soc. 143 (2021) 1313–1317. doi: 10.1021/jacs.0c12522
15. [15]
  Y. Li, S.S. Rajasree, G.Y. Lee, et al., J. Am. Chem. Soc. 143 (2021) 2908–2919. doi: 10.1021/jacs.0c12853
16. [16]
  Z. Zhang, Z. Zhao, Y. Hou, et al., Angew. Chem. Int. Ed. 58 (2019) 8862–8866. doi: 10.1002/anie.201904407
17. [17]
  T. Xiao, D. Chen, H. Qian, et al., Dyes Pigments 210 (2023) 110958. doi: 10.1016/j.dyepig.2022.110958
18. [18]
  T. Xiao, H. Qian, Y. Shen, et al., Mater. Today Chem. 24 (2022) 100833. doi: 10.1016/j.mtchem.2022.100833
19. [19]
  G. Sun, L. Cai, H. Cui, et al., Dyes Pigments 201 (2022) 110257. doi: 10.1016/j.dyepig.2022.110257
20. [20]
  X.M. Chen, K.W. Cao, H.K. Bisoyi, et al., Small 18 (2022) e2204360. doi: 10.1002/smll.202204360
21. [21]
  L. Xu, Z. Wang, R. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 9908–9913. doi: 10.1002/anie.201907678
22. [22]
  X.H. Wang, N. Song, W. Hou, et al., Adv. Mater. 31 (2019) 1903962. doi: 10.1002/adma.201903962
23. [23]
  J.J. Li, Y. Chen, J. Yu, et al., Adv. Mater. 29 (2017) 1701905. doi: 10.1002/adma.201701905
24. [24]
  P. Ensslen, H.A. Wagenknecht, Acc. Chem. Res. 48 (2015) 2724–2733. doi: 10.1021/acs.accounts.5b00314
25. [25]
  P.K. Dutta, R. Varghese, J. Nangreave, et al., J. Am. Chem. Soc. 133 (2011) 11985–11993. doi: 10.1021/ja1115138
26. [26]
  A. Nandy, S. Mukherjee, J. Phys. Chem. Lett. 13 (2022) 6701–6710. doi: 10.1021/acs.jpclett.2c01309
27. [27]
  Q. Song, S. Goia, J. Yang, et al., J. Am. Chem. Soc. 143 (2021) 382–389. doi: 10.1021/jacs.0c11060
28. [28]
  S. Hirayama, K. Oohora, T. Uchihashi, et al., J. Am. Chem. Soc. 142 (2020) 1822–1831. doi: 10.1021/jacs.9b10080
29. [29]
  F. Würthner, Angew. Chem. Int. Ed. 59 (2020) 14192–14196. doi: 10.1002/anie.202007525
30. [30]
  Y. Hong, J.W.Y. Lam, B.Z. Tang, Chem. Soc. Rev. 40 (2011) 5361–5388. doi: 10.1039/c1cs15113d
31. [31]
  Y.X. Yuan, J.H. Jia, Y.P. Song, et al., J. Am. Chem. Soc. 144 (2022) 5389–5399. doi: 10.1021/jacs.1c12767
32. [32]
  T. Xiao, C. Bao, L. Zhang, et al., J. Mater. Chem. A 10 (2022) 8528–8534. doi: 10.1039/d2ta00277a
33. [33]
  C.Q. Ma, X.L. Li, N. Han, et al., J. Mater. Chem. A 10 (2022) 16390–16395. doi: 10.1039/d2ta04124c
34. [34]
  X. Zhu, J.X. Wang, L.Y. Niu, et al., Chem. Mater. 31 (2019) 3573–3581. doi: 10.1021/acs.chemmater.9b01338
35. [35]
  Y. Li, Y. Dong, L. Cheng, et al., J. Am. Chem. Soc. 141 (2019) 8412–8415. doi: 10.1021/jacs.9b02617
36. [36]
  W. Zhang, Y. Luo, X.L. Ni, et al., Chem. Eng. J. 446 (2022) 136954. doi: 10.1016/j.cej.2022.136954
37. [37]
  Y. Li, C. Xia, R. Tian, et al., ACS Nano 16 (2022) 8012–8021. doi: 10.1021/acsnano.2c00960
38. [38]
  T. Xiao, L. Zhang, H. Wu, et al., Chem. Commun. 57 (2021) 5782–5785. doi: 10.1039/d1cc01788h
39. [39]
  P.P. Jia, L. Xu, Y.X. Hu, et al., J. Am. Chem. Soc. 143 (2021) 399–408. doi: 10.1021/jacs.0c11370
40. [40]
  G. Sun, W. Qian, J. Jiao, et al., J. Mater. Chem. A 8 (2020) 9590–9596. doi: 10.1039/d0ta03169k
41. [41]
  J.J. Li, H.Y. Zhang, X.Y. Dai, et al., Chem. Commun. 56 (2020) 5949–5952. doi: 10.1039/d0cc01292k
42. [42]
  M. Hao, G. Sun, M. Zuo, et al., Angew. Chem. Int. Ed. 59 (2020) 10095–10100. doi: 10.1002/anie.201912654
43. [43]
  L. Ji, Y. Sang, G. Ouyang, et al., Angew. Chem. Int. Ed. 58 (2019) 844–848. doi: 10.1002/anie.201812642
44. [44]
  T. Xiao, J. Wang, Y. Shen, et al., Chin. Chem. Lett. 32 (2021) 1377–1380. doi: 10.1016/j.cclet.2020.10.037
45. [45]
  T. Xiao, L. Zhou, X.Q. Sun, et al., Chin. Chem. Lett. 31 (2020) 1–9. doi: 10.1016/j.cclet.2019.05.011
46. [46]
  M. Wehner, F. Würthner, Nat. Rev. Chem. 4 (2020) 38–53.
47. [47]
  E. Krieg, M.M.C. Bastings, P. Besenius, et al., Chem. Rev. 116 (2016) 2414–2477. doi: 10.1021/acs.chemrev.5b00369
48. [48]
  L. Yang, X. Tan, Z. Wang, et al., Chem. Rev. 115 (2015) 7196–7239. doi: 10.1021/cr500633b
49. [49]
  X. Yan, F. Wang, B. Zheng, et al., Chem. Soc. Rev. 41 (2012) 6042–6065. doi: 10.1039/c2cs35091b
50. [50]
  T. Aida, E.W. Meijer, S.I. Stupp, Science 335 (2012) 813–817. doi: 10.1126/science.1205962
51. [51]
  X.H. Wang, X.Y. Lou, T. Lu, et al., ACS Appl. Mater. Interfaces 13 (2021) 4593–4604. doi: 10.1021/acsami.0c21651
52. [52]
  Y. Han, X. Zhang, Z. Ge, et al., Nat. Commun. 13 (2022) 3546. doi: 10.1038/s41467-022-31094-w
53. [53]
  T. Aida, Adv. Mater. 32 (2020) e1905445. doi: 10.1002/adma.201905445
54. [54]
  R.P. Sijbesma, F.H. Beijer, L. Brunsveld, et al., Science 278 (1997) 1601–1604. doi: 10.1126/science.278.5343.1601
55. [55]
  T. Xiao, W. Zhong, W. Yang, et al., Chem. Commun. 56 (2020) 14385–14388. doi: 10.1039/d0cc06381a
56. [56]
  K.X. Teng, L.Y. Niu, N. Xie, et al., Nat. Commun. 13 (2022) 6179. doi: 10.1038/s41467-022-33924-3
57. [57]
  T. Xiao, L. Zhou, L. Xu, et al., Chin. Chem. Lett. 30 (2019) 271–276. doi: 10.1016/j.cclet.2018.05.039
58. [58]
  T. Xiao, L. Xu, L. Zhou, et al., J. Mater. Chem. B 7 (2019) 1526–1540. doi: 10.1039/c8tb02339e
59. [59]
  M. Cheng, D. Chen, L. Zhang, et al., Org. Chem. Front. 10 (2023) 1380–1385. doi: 10.1039/d2qo01888h
60. [60]
  T. Xiao, L. Tang, D. Ren, et al., Chem. Eur. J. 29 (2023) e202203463. doi: 10.1002/chem.202203463
61. [61]
  K. Diao, D.J. Whitaker, Z. Huang, et al., Chem. Commun. 58 (2022) 2343–2346. doi: 10.1039/d1cc06647a
62. [62]
  C.L. Sun, H.Q. Peng, L.Y. Niu, et al., Chem. Commun. 54 (2018) 1117–1120. doi: 10.1039/C7CC09315B
63. [63]
  H.Q. Peng, J.F. Xu, Y.Z. Chen, et al., Chem. Commun. 50 (2014) 1334–1337. doi: 10.1039/C3CC48618D
64. [64]
  D. Li, J. Wang, X. Ma, Adv. Opt. Mater. 6 (2018) 1800273. doi: 10.1002/adom.201800273
65. [65]
  X. Zhang, D. Görl, F. Würthner, Chem. Commun. 49 (2013) 8178–8180. doi: 10.1039/c3cc44875d
66. [66]
  H.T. Feng, X. Zheng, X. Gu, et al., Chem. Mater. 30 (2018) 1285–1290. doi: 10.1021/acs.chemmater.7b04703
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