Citation: Dongxing Ren, Lu Tang, Zhiying Wu, Qiaona Zhang, Tangxin Xiao, Robert B.P. Elmes, Leyong Wang. An amphiphilic molecule with a single fluorophore exhibits multiple stimuli-responsive behavior[J]. Chinese Chemical Letters, ;2023, 34(11): 108617. doi: 10.1016/j.cclet.2023.108617 shu

An amphiphilic molecule with a single fluorophore exhibits multiple stimuli-responsive behavior

a.
School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
b.
Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Co. Kildare, Ireland
c.
Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China

^☆

^th

xiaotangxin@cczu.edu.cn

Received Date: 24 March 2023
Revised Date: 19 May 2023
Accepted Date: 24 May 2023
Available Online: 26 May 2023

Figures(5)

Fluorescent materials that respond to multiple stimuli have broad applications ranging from sensing and bioimaging to information encryption. Herein, we report the design and synthesis of a single-fluorophore-based amphiphile DCSO, which shows temperature-, solvent-, humidity-, and radiation-dependent fluorescence. DCSO consists of a dicyanostilbene (DCS) group as a rigid hydrophobic core with oligo(ethylene glycol) (OEG) chains at both ends as a flexible hydrophilic periphery. The DCS group acts as a highly efficient fluorophore, while the OEG chain endows the molecule with thermo-responsiveness. Fluorescent colors can vary from blue to green to yellow in response to external stimuli. On the basis of light radiation, we demonstrate that this system can be applied to time-dependent information encryption, in which the correct information can only be read at a specific time under irradiation. This work further demonstrates the usefulness and application of single-fluorophore-based luminescent materials with multiple stimuli-responsive functions.
- Self-assembly,
- Multi-responsive fluorescence,
- Single fluorophore,
- Information encryption,
- Smart materials
1. [1]
  G. Isapour, M. Lattuada, Adv. Mater. 30 (2018) 1707069. doi: 10.1002/adma.201707069
2. [2]
  Y. Wang, H. Cui, Q. Zhao, et al., Matter 1 (2019) 626–638. doi: 10.1016/j.matt.2019.05.012
3. [3]
  H.H. Chou, A. Nguyen, A. Chortos, et al., Nat. Commun. 6 (2015) 8011. doi: 10.1038/ncomms9011
4. [4]
  X. Zhang, L. Chen, K.H. Lim, et al., Adv. Mater. 31 (2019) 1804540. doi: 10.1002/adma.201804540
5. [5]
  P. Theato, B.S. Sumerlin, R.K. O'Reilly, et al., Chem. Soc. Rev. 42 (2013) 7055–7056. doi: 10.1039/c3cs90057f
6. [6]
  S. Mura, J. Nicolas, P. Couvreur, Nat. Mater. 12 (2013) 991–1003. doi: 10.1038/nmat3776
7. [7]
  D. Roy, J.N. Cambre, B.S. Sumerlin, Prog. Polym. Sci. 35 (2010) 278–301. doi: 10.1016/j.progpolymsci.2009.10.008
8. [8]
  J. Zhang, B. He, Y. Hu, et al., Adv. Mater. 33 (2021) 2008071. doi: 10.1002/adma.202008071
9. [9]
  H. Duan, F. Cao, M. Zhang, et al., Chin. Chem. Lett. 33 (2022) 2459–2463. doi: 10.1016/j.cclet.2021.11.010
10. [10]
  B. Lu, S. Liu, D. Yan, Chin. Chem. Lett. 30 (2019) 1908–1922. doi: 10.1016/j.cclet.2019.09.012
11. [11]
  Z. Guo, G. Li, H. Wang, et al., J. Am. Chem. Soc. 143 (2021) 9215–9221. doi: 10.1021/jacs.1c04288
12. [12]
  T. Xiao, J. Wang, Y. Shen, et al., Chin. Chem. Lett. 32 (2021) 1377–1380. doi: 10.1016/j.cclet.2020.10.037
13. [13]
  Z. Cao, D. Wu, M. Li, et al., Chin. Chem. Lett. 33 (2022) 1533–1536. doi: 10.1016/j.cclet.2021.09.001
14. [14]
  K. Lou, Z. Hu, H. Zhang, et al., Adv. Funct. Mater. 32 (2022) 2113274. doi: 10.1002/adfm.202113274
15. [15]
  T. Chen, Y.J. Ma, D. Yan, Adv. Funct. Mater. 33 (2023) 2214962. doi: 10.1002/adfm.202214962
16. [16]
  Y.J. Ma, G. Xiao, X. Fang, et al., Angew. Chem. Int. Ed. 62 (2023) e202217054. doi: 10.1002/anie.202217054
17. [17]
  Z. Wang, L. Gao, Y. Zheng, et al., Angew. Chem. Int. Ed. 61 (2022) e202203254. doi: 10.1002/anie.202203254
18. [18]
  W. Luo, G. Wang, Adv. Opt. Mater. 8 (2020) 2001362. doi: 10.1002/adom.202001362
19. [19]
  Z. Yang, Z. Chi, Z. Mao, et al., Mater. Chem. Front. 2 (2018) 861–890. doi: 10.1039/C8QM00062J
20. [20]
  J. Zhou, B. del Rosal, D. Jaque, et al., Nat. Methods 17 (2020) 967–980. doi: 10.1038/s41592-020-0957-y
21. [21]
  M. Luo, X. Li, L. Ding, et al., Angew. Chem. Int. Ed. 59 (2020) 17018–17025. doi: 10.1002/anie.202009077
22. [22]
  H. Xiao, P. Li, B. Tang, Coord. Chem. Rev. 427 (2021) 213582. doi: 10.1016/j.ccr.2020.213582
23. [23]
  R. Huang, C. Wang, D. Tan, et al., Angew. Chem. Int. Ed. 61 (2022) e202211106. doi: 10.1002/anie.202211106
24. [24]
  S.H. Hwang, H. Kim, H. Ryu, et al., J. Am. Chem. Soc. 144 (2022) 1778–1785. doi: 10.1021/jacs.1c11100
25. [25]
  Q. Wang, Q. Zhang, Q.W. Zhang, et al., Nat. Commun. 11 (2020) 158. doi: 10.1038/s41467-019-13994-6
26. [26]
  P.F. Wei, T.R. Cook, X.H. Yan, et al., J. Am. Chem. Soc. 136 (2014) 15497–15500. doi: 10.1021/ja5093503
27. [27]
  D. Görl, B. Soberats, S. Herbst, et al., Chem. Sci. 7 (2016) 6786–6790. doi: 10.1039/C6SC02249A
28. [28]
  H.Q. Peng, B. Liu, P. Wei, et al., ACS Nano 13 (2019) 839–846. doi: 10.1021/acsnano.8b08358
29. [29]
  T. Xiao, L. Zhou, L. Xu, et al., Chin. Chem. Lett. 30 (2019) 271–276. doi: 10.1016/j.cclet.2018.05.039
30. [30]
  Y. Cai, Z. Zhang, Y. Ding, et al., Chin. Chem. Lett. 32 (2021) 1267–1279. doi: 10.1016/j.cclet.2020.10.036
31. [31]
  Q. Zhang, S. Dong, M. Zhang, et al., Aggregate 2 (2021) 35–47. doi: 10.1002/agt2.12
32. [32]
  T. Xiao, L. Tang, D. Ren, et al., Chem. Eur. J. 29 (2023) e202203463. doi: 10.1002/chem.202203463
33. [33]
  T. Xiao, D. Ren, K. Diao, et al., Chem. Asian J. 17 (2022) e202200386. doi: 10.1002/asia.202200386
34. [34]
  Q. Wang, Z. Qi, Q.M. Wang, et al., Adv. Funct. Mater. 32 (2022) 2208865. doi: 10.1002/adfm.202208865
35. [35]
  Y. Deng, X. Li, C.Y. Han, et al., Chin. Chem. Lett. 31 (2020) 3221–3224. doi: 10.1016/j.cclet.2020.03.074
36. [36]
  S. Wang, Z. Xu, T. Wang, et al., Nat. Commun. 9 (2018) 1737. doi: 10.1038/s41467-018-03827-3
37. [37]
  D. Görl, F. Würthner, Angew. Chem. Int. Ed. 55 (2016) 12094–12098. doi: 10.1002/anie.201606917
38. [38]
  Z. Li, Z. Yang, Y. Zhang, et al., Angew. Chem. Int. Ed. 61 (2022) e202206144. doi: 10.1002/anie.202206144
39. [39]
  T. Dünnebacke, K.K. Kartha, J.M. Wahl, et al., Chem. Sci. 11 (2020) 10405–10413. doi: 10.1039/d0sc03442h
40. [40]
  L. Ascherl, E.W. Evans, M. Hennemann, et al., Nat. Commun. 9 (2018) 3802. doi: 10.1038/s41467-018-06161-w
41. [41]
  Z.Z. Lu, R. Zhang, Y.Z. Li, et al., J. Am. Chem. Soc. 133 (2011) 4172–4174. doi: 10.1021/ja109437d
42. [42]
  J.H. Kim, T. Schembri, D. Bialas, et al., Adv. Mater. 34 (2022) e2104678. doi: 10.1002/adma.202104678
43. [43]
  X. Yang, S. Liu, Dyes Pigm. 159 (2018) 331–336. doi: 10.1016/j.dyepig.2018.06.027
44. [44]
  K. Cai, J. Xie, D. Zhao, J. Am. Chem. Soc. 136 (2014) 28–31. doi: 10.1021/ja410265n
45. [45]
  J.L. Belmonte-Vázquez, Y.A. Amador-Sánchez, L.A. Rodríguez-Cortés, et al., Chem. Mater. 33 (2021) 7160–7184. doi: 10.1021/acs.chemmater.1c02460
46. [46]
  L.A. Rodríguez-Cortés, A. Navarro-Huerta, B. Rodríguez-Molina, Matter 4 (2021) 2622–2624. doi: 10.1016/j.matt.2021.06.023
47. [47]
  Y. Xue, S. Jiang, H. Zhong, et al., Angew. Chem. Int. Ed. 61 (2022) e202110766. doi: 10.1002/anie.202110766
48. [48]
  S.K. Bhaumik, S. Banerjee, ACS Appl. Mater. Interfaces 14 (2022) 36936–36946. doi: 10.1021/acsami.2c07836
49. [49]
  P. Wei, J.X. Zhang, Z. Zhao, et al., J. Am. Chem. Soc. 140 (2018) 1966–1975. doi: 10.1021/jacs.7b13364
50. [50]
  Y. Zhang, X. Zhang, Z. Feng, et al., ACS Appl. Mater. Interfaces 13 (2021) 44797–44805. doi: 10.1021/acsami.1c12647
51. [51]
  Z. Zong, Q. Zhang, D.H. Qu, Chem. Eur. J. 28 (2022) e202202462. doi: 10.1002/chem.202202462
52. [52]
  S. Liu, Y. Lin, D. Yan, Sci. Bull. 67 (2022) 2076–2084. doi: 10.1016/j.scib.2022.09.025
53. [53]
  F. Nie, B. Zhou, K.Z. Wang, et al., Chem. Eng. J. 430 (2022) 133084. doi: 10.1016/j.cej.2021.133084
54. [54]
  F. Nie, K.Z. Wang, D. Yan, Nat. Commun. 14 (2023) 1654. doi: 10.1038/s41467-023-37331-0
1. [1]
  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
2. [2]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
3. [3]
  Jingqi Xin , Shupeng Han , Meichen Zheng , Chenfeng Xu , Zhongxi Huang , Bin Wang , Changmin Yu , Feifei An , Yu Ren . A nitroreductase-responsive nanoprobe with homogeneous composition and high loading for preoperative non-invasive tumor imaging and intraoperative guidance. Chinese Chemical Letters, 2024, 35(7): 109165-. doi: 10.1016/j.cclet.2023.109165
4. [4]
  Keyang Li , Yanan Wang , Yatao Xu , Guohua Shi , Sixian Wei , Xue Zhang , Baomei Zhang , Qiang Jia , Huanhua Xu , Liangmin Yu , Jun Wu , Zhiyu He . Flash nanocomplexation (FNC): A new microvolume mixing method for nanomedicine formulation. Chinese Chemical Letters, 2024, 35(10): 109511-. doi: 10.1016/j.cclet.2024.109511
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]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
7. [7]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
8. [8]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
9. [9]
  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
10. [10]
  Minghao Hu , Tianci Xie , Yuqiang Hu , Longjie Li , Ting Wang , Tongbo Wu . Allosteric DNAzyme-based encoder for molecular information transfer. Chinese Chemical Letters, 2024, 35(7): 109232-. doi: 10.1016/j.cclet.2023.109232
11. [11]
  Hang Meng , Bicheng Zhu , Ruolun Sun , Zixuan Liu , Shaowen Cao , Kan Zhang , Jiaguo Yu , Jingsan Xu . Dynamic photoluminescence switching of carbon nitride thin films for anticounterfeiting and encryption. Chinese Journal of Structural Chemistry, 2024, 43(10): 100410-100410. doi: 10.1016/j.cjsc.2024.100410
12. [12]
  Lumin Zheng , Ying Bai , Chuan Wu . Multi-electron reaction and fast Al ion diffusion of δ-MnO₂ cathode materials in rechargeable aluminum batteries via first-principle calculations. Chinese Chemical Letters, 2024, 35(4): 108589-. doi: 10.1016/j.cclet.2023.108589
13. [13]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
14. [14]
  Shaohua Zhang , Liyao Liu , Yingqiao Ma , Chong-an Di . Advances in theoretical calculations of organic thermoelectric materials. Chinese Chemical Letters, 2024, 35(8): 109749-. doi: 10.1016/j.cclet.2024.109749
15. [15]
  Junjie Wang , Yan Wang , Zhengdong Li , Changqiang Xie , Musammir Khan , Xingzhou Peng , Fabiao Yu . Triphenylamine-AIEgens photoactive materials for cancer theranostics. Chinese Chemical Letters, 2024, 35(6): 108934-. doi: 10.1016/j.cclet.2023.108934
16. [16]
  Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
17. [17]
  Yukai Tong , Zhijun Wu , Bo Zhou , Min Hu , Anpei Ye . Surface tension of single suspended aerosol microdroplets. Chinese Chemical Letters, 2024, 35(4): 109062-. doi: 10.1016/j.cclet.2023.109062
18. [18]
  Kun Tang , Yu-Wu Zhong . Water reduction by an organic single-chromophore photocatalyst. Chinese Journal of Structural Chemistry, 2024, 43(8): 100376-100376. doi: 10.1016/j.cjsc.2024.100376
19. [19]
  Rui PAN , Yuting MENG , Ruigang XIE , Daixiang CHEN , Jiefa SHEN , Shenghu YAN , Jianwu LIU , Yue ZHANG . Selective electrocatalytic reduction of Sn(Ⅳ) by carbon nitrogen materials prepared with different precursors. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1015-1024. doi: 10.11862/CJIC.20230433
20. [20]
  Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(301)
HTML views(8)

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