Citation: Kai An, Qinglong Qiao, Lovelesh, Syed Ali Abbas Abedi, Xiaogang Liu, Zhaochao Xu. "Superimposed" spectral characteristics of fluorophores arising from cross-conjugation hybridization[J]. Chinese Chemical Letters, ;2025, 36(1): 109786. doi: 10.1016/j.cclet.2024.109786 shu

"Superimposed" spectral characteristics of fluorophores arising from cross-conjugation hybridization

Kai An ^{a, b} ,
Qinglong Qiao ^a ,
Lovelesh ^c ,
Syed Ali Abbas Abedi ^c ,
Xiaogang Liu ^{c, *,} ,
Zhaochao Xu ^{a, b, *,}

a.
CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
Fluorescence Research Group, Singapore University of Technology and Design, Singapore 487372, Singapore

xiaogang_liu@sutd.edu.sg

zcxu@dicp.ac.cn

Received Date: 10 March 2024
Revised Date: 15 March 2024
Accepted Date: 18 March 2024
Available Online: 18 March 2024

Figures(4)

The demand for enhanced optical properties in advanced fluorescence technologies has driven research into the structure-property relationship of fluorophores. In this paper, we use naphthalene fluorophores NaDC-Aze and PhDO-Aze as a case study to emphasize the pivotal role of cross conjugation in tuning the optical structure-property relationship. NaDC-Aze and PhDO-Aze, formed by hybridizing two distinct conjugated systems in a single naphthalene molecule, exhibit spectral characteristics from both conjugated systems. Experimental data and theoretical calculations demonstrate the coexistence of two electron-delocalization systems in a cross-conjugation manner in both NaDC-Aze and PhDO-Aze. The cross-conjugation fluorophores exhibit high brightness, large Stokes shift, and a broad absorption wavelength range by combining distinct spectral properties from its parent fluorophores. These spectral properties will be advantageous for certain applications (i.e., panchromatic absorption in organic solar cells, and fluorophores compatible with a wide range of excitation wavelengths).
- Fluorophore,
- Cross conjugation,
- Absorption,
- Emission,
- Naphthalene
1. [1]
  R.W. Sinkeldam, N.J. Greco, Y. Tor, Chem. Rev. 110 (2010) 2579–2619. doi: 10.1021/cr900301e
2. [2]
  E.M.S. Stennett, M.A. Ciuba, M. Levitus, Chem. Soc. Rev. 43 (2014) 1057–1075. doi: 10.1039/C3CS60211G
3. [3]
  A. Kurutos, D. Citterio, J. Mol. Struct. 1247 (2022) 131381. doi: 10.1016/j.molstruc.2021.131381
4. [4]
  J.V. Jun, E.J. Petersson, D.M. Chenoweth, J. Am. Chem. Soc. 140 (2018) 9486–9493. doi: 10.1021/jacs.8b03738
5. [5]
  M. Pengshung, P. Neal, T.L. Atallah, et al., Chem. Commun. 56 (2020) 6110–6113. doi: 10.1039/c9cc09671j
6. [6]
  C.X. Yan, Z.Q. Guo, W.J. Chi, et al., Nat. Commun. 12 (2021) 3869. doi: 10.1038/s41467-021-24187-5
7. [7]
  C.S. Abeywickrama, Chem. Commun. 58 (2022) 9855–9869. doi: 10.1039/d2cc03880c
8. [8]
  X. Cheng, S. Huang, Q. Lei, et al., Chin. Chem. Lett. 33 (2022) 1861–1864. doi: 10.1016/j.cclet.2021.10.024
9. [9]
  W. Chi, Q. Qiao, C. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 20215–20223. doi: 10.1002/anie.202010169
10. [10]
  X.G. Liu, Q.L. Qiao, W.M. Tian, et al., J. Am. Chem. Soc. 138 (2016) 6960–6963. doi: 10.1021/jacs.6b03924
11. [11]
  Z.G. Yang, A. Sharma, J. Qi, et al., Chem. Soc. Rev. 45 (2016) 4651–4667. doi: 10.1039/C5CS00875A
12. [12]
  C.Y. Li, G.C. Chen, Y.J. Zhang, et al., J. Am. Chem. Soc. 142 (2020) 14789–14804. doi: 10.1021/jacs.0c07022
13. [13]
  Q.L. Qiao, W.J. Liu, J. Chen, et al., Angew. Chem. Int. Ed. 61 (2022) e202202961. doi: 10.1002/anie.202202961
14. [14]
  J. Chen, W.J. Liu, X.N. Fang, et al., Chin. Chem. Lett. 33 (2022) 5042–5046. doi: 10.1016/j.cclet.2022.03.120
15. [15]
  J.J. Yim, S. Harmsen, K. Flisikowski, et al., Proc. Natl. Acad. Sci. U. S. A. 118 (2020) e2008072118.
16. [16]
  X. Zhao, Q.C. Yao, S. Long, et al., J. Am. Chem. Soc. 143 (2021) 12345–12354. doi: 10.1021/jacs.1c06275
17. [17]
  C.E. Yang, H.R. Wang, S. Yokomizo, et al., Angew. Chem. Int. Ed. 60 (2021) 13847–13852. doi: 10.1002/anie.202102640
18. [18]
  W.J. Liu, J. Chen, Q.L. Qiao, et al., Chin. Chem. Lett. 33 (2022) 4943–4947. doi: 10.1016/j.cclet.2022.03.121
19. [19]
  Z.F. Li, Q.L. Qiao, N. Xu, et al., Chin. Chem. Lett. 35 (2024) 108824. doi: 10.1016/j.cclet.2023.108824
20. [20]
  J. Li, Q.L. Qiao, Y.Y. Ruan, et al., Chin. Chem. Lett. 34 (2023) 108266. doi: 10.1016/j.cclet.2023.108266
21. [21]
  J.P. Ding, R.S. Xiao, A.Y. Bi, et al., Chin. Chem. Lett. 34 (2023) 108273. doi: 10.1016/j.cclet.2023.108273
22. [22]
  T. Beppu, K. Tomiguchi, A. Masuhara, et al., Angew. Chem. Int. Ed. 54 (2015) 7332–7335. doi: 10.1002/anie.201502365
23. [23]
  H. John, C. Briehn, J. Schmidt, et al., Angew. Chem. Int. Ed. 46 (2007) 449–453. doi: 10.1002/anie.200602596
24. [24]
  X. Wu, D. Tan, Q.L. Qiao, et al., Phys. Chem. Chem. Phys. 24 (2022) 15937–15944. doi: 10.1039/d2cp00759b
25. [25]
  X.G. Liu, J.M. Cole, Z.C. Xu, J. Phys. Chem. C 121 (2017) 13274–13279. doi: 10.1021/acs.jpcc.7b04176
26. [26]
  J. Chen, C. Wang, W.J. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 25104–25113. doi: 10.1002/anie.202111052
27. [27]
  W. Zhou, Q.L. Qiao, Y. Tao, et al., Sens. Actuat. B: Chem. 376 (2023) 132980. doi: 10.1016/j.snb.2022.132980
28. [28]
  N. Xu, Q.L. Qiao, J. Chen, et al., Chem. Commun. 60 (2024) 1424–1427. doi: 10.1039/d3cc05853k
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