Citation: Yanqi Ban, Linhong Hao, Zhenbo Peng, Lishui Sun, Lihua Teng, Yingjie Zhao. Triphenylamine-based highly active two-photon absorbing chromophores with push-pull systems[J]. Chinese Chemical Letters, ;2023, 34(7): 107880. doi: 10.1016/j.cclet.2022.107880 shu

Triphenylamine-based highly active two-photon absorbing chromophores with push-pull systems

a.
College of Polymer Science and Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
b.
College of Mathematics and Physics, Qingdao University of Science and Technology, Qingdao 266061, China

Received Date: 5 July 2022
Revised Date: 31 August 2022
Accepted Date: 4 October 2022
Available Online: 9 October 2022

Figures(4)

Two triphenylamine-based star-type push-pull chromophores (T1, T2) were designed and synthesized. Triphenylamine serves as the central core and acts as an electron-donating group surrounded by electron-withdrawing pentafluorobenzene or N, N-dimethyl substituted tetrafluorobenzene, which are connected by ethylene bridges. Single-crystal X-ray diffraction confirmed the structures and molecular arrangement of two chromophores. The systematic photophysical research of T1 and T2 absorption characteristics was carried out to gain a better understanding of how structure-property relationships affect the observed nonlinear optical absorption phenomenon. Complementary calculations based on density functional theory (DFT) further confirmed the experimental results. Both chromophores exhibited excellent two-photon absorption (TPA) properties in CH₂Cl₂. Notably, T2 has more remarkable nonlinear optical absorption effects with the TPA cross-section up to 4.24 × 10⁷ GM. By adjusting the electronic structures of the chromophores through introducing pentafluorobenzene or N, N-dimethyl as functional groups with different electron-donating or withdrawing behaviors, the TPA performance of the small organic molecule could be greatly enhanced. These molecular structures with push-pull systems were excellent candidates for different two-photon applications.
- Star-type chromophores,
- Triphenylamine derivatives,
- Two-photon absorption,
- Nonlinear optical materials,
- Push-pull systems
1. [1]
  M. Pawlicki, H.A. Collins, R.G. Denning, H.L. Anderson, Angew. Chem. Int. Ed. 48 (2009) 3244–3266. doi: 10.1002/anie.200805257
2. [2]
  L. Liu, Z.Q. Zhou, J.P. Shi, et al., Chin. Chem. Lett. 22 (2011) 1147–1150. doi: 10.1016/j.bmcl.2012.07.033
3. [3]
  L. Porre's, O. Mongin, C. Katan, et al., Org. Lett. 6 (2004) 47–50. doi: 10.1021/ol036041s
4. [4]
  P. Wei, X.D. Bi, Z. Wu, Z. Xu, Org. Lett. 7 (2005) 3199–3202. doi: 10.1021/ol050905n
5. [5]
  O. Mongin, L. Porre's, C. Katan, et al., Tetrahedron Lett. 44 (2003) 8121–8125. doi: 10.1016/j.tetlet.2003.09.025
6. [6]
  B.P. Biswal, S. Valligatla, M. Wang, et al., Angew. Chem. Int. Ed. 58 (2019) 6896–6900. doi: 10.1002/anie.201814412
7. [7]
  M. Hansel, C. Barta, C. Rietze, et al., J. Phys. Chem. C 122 (2018) 25555–25564. doi: 10.1021/acs.jpcc.8b08212
8. [8]
  U.R. Felscia, B.J.M. Rajkumar, P. Sankar, R. Philip, M.B. Mary, Mater. Chem. Phys. 243 (2020) 122466. doi: 10.1016/j.matchemphys.2019.122466
9. [9]
  W. Zhuang, L. Yang, B, Ma, et al., ACS Appl. Mater. Interfaces 11 (2019) 20715–20724. doi: 10.1021/acsami.9b04813
10. [10]
  K.A. Kasischke, H.D. Vishwasrao, P.J. Fisher, W.R. Zipfel, W.W. Webb, Science 305 (2004) 99–103. doi: 10.1126/science.1096485
11. [11]
  X. Li, Z. Li; Y.W. Yang, Adv. Mater. 30 (2018) 1800177. doi: 10.1002/adma.201800177
12. [12]
  C. Katan, F. Terenziani, O. Mongin, J. Phys. Chem. 109 (2005) 3024–3037. doi: 10.1021/jp044193e
13. [13]
  H.M. Kim, B.R. Cho. Chem. Commun. 2 (2009) 153–164. doi: 10.1039/b813280a
14. [14]
  F. Terenziani, C.L. Droumaguet, C. Katan, O. Mongin, M.B. Desce, Chem. Phys. Chem. 8 (2007) 723–734. doi: 10.1002/cphc.200600689
15. [15]
  H. Detert, M. Lehmann, H. Meier. Materials 3 (2010) 3218–3330. doi: 10.3390/ma3053218
16. [16]
  M. Drobizhev, A. Karotki, Y. Dzenis, et al., J. Phys. Chem. B 107 (2003) 7540–7543. doi: 10.1021/jp034986l
17. [17]
  V. Anand, B. Sadhasivam, R. Dhamodharan. New J. Chem. 42 (2018) 18979–18990. doi: 10.1039/c8nj03316a
18. [18]
  E. Piovesan, L.B. Boni, E. Ishow, C.R. Mendonca, Chem. Phys. Lett. 498 (2010) 277–280. doi: 10.1016/j.cplett.2010.08.080
19. [19]
  R. Lartia, C. Allain, G. Bordeau, et al., J. Org. Chem. 73 (2008) 1732–1744. doi: 10.1021/jo702002y
20. [20]
  X. Gan, Y. Wang, X. Ge, et al., Dye. Pigment. 120 (2015) 65–73. doi: 10.1016/j.dyepig.2015.04.007
21. [21]
  T. Ishii, T. Isozaki, S. Kinoshita, et al., J. Phys. Chem. A 125 (2021) 1688–1695. doi: 10.1021/acs.jpca.0c10545
22. [22]
  Y. Gong, G.L. Hou, X. Bi, et al., J. Phys. Chem. A 125 (2021) 1870–1879. doi: 10.1021/acs.jpca.0c10567
23. [23]
  H. Chen, L. Wang, W. Wang, et al., RSC Adv. 6 (2016) 97063–97069. doi: 10.1039/C6RA22020G
24. [24]
  W. Deng, H. Qu, Z. Huang, et al., Chem. Commun. 55 (2019) 2210–2213. doi: 10.1039/c8cc08947g
25. [25]
  S.R. Marder, L.T. Cheng, B.G. Tiemann, et al., Science. 263 (1994) 511–514. doi: 10.1126/science.263.5146.511
26. [26]
  T. Kim, K Lee, Macromol. Rapid Commun. 36 (2015) 943–958. doi: 10.1002/marc.201400749
27. [27]
  A. Mishra, M.K.R. Fischer, P. Bauerle, Angew. Chem. Int. Ed. 48 (2009), 2474–2499. doi: 10.1002/anie.200804709
28. [28]
  Y. Zhang, J. Guo, X. Li, et al., Spectrochim Acta Part A 230 (2020) 118015. doi: 10.1016/j.saa.2019.118015
29. [29]
  X. Zhang, X. Gan, S. Yao, et al., RSC Adv. 6 (2016) 60022–60028 doi: 10.1039/C6RA09701D
30. [30]
  C.L. Devi, K. Yesudas, N.S. Makarov, et al., Dye. Pigment. 113 (2015) 682–691. doi: 10.1016/j.dyepig.2014.09.027
31. [31]
  F. Ricci, F. Elisei, P. Foggi, et al., J. Phys. Chem. C 120 (2016) 23726–23739. doi: 10.1021/acs.jpcc.6b07290
32. [32]
  B. Dereka, M. Koch, E. Vauthey, Acc. Chem. Res. 50 (2017) 426–434. doi: 10.1021/acs.accounts.6b00538
33. [33]
  B. An, J. Gierschner, S. Park, Acc. Chem. Res. 45 (2012) 544–554. doi: 10.1021/ar2001952
34. [34]
  M. Klikar, D. Georgiou, I. Polyzos, et al., Dye. Pigment. 201 (2022) 110230. doi: 10.1016/j.dyepig.2022.110230
35. [35]
  J. Wei, Y. Li, P. Song, F. Ma, J. Phys. Chem. A 125 (2021) 777–794. doi: 10.1021/acs.jpca.0c09309
36. [36]
  A. Shabashini, V. Ramar, B. Karthikeyan, M.K. Panda, G.C. Nandi, ChemistrySelect 6 (2021) 12300–12308. doi: 10.1002/slct.202103085
37. [37]
  M.M. Raikwar, E. Mathew, M. Varghese, I.H. Joe, S.N. Nethi, Photochem. Photobiol. 95 (2019) 931–945. doi: 10.1016/j.jphotochem.2018.12.035
38. [38]
  R.D. Mohbiya, R.R. Mallah, M.C. Sreenath, et al., Opt. Mater. 89 (2019) 178–190. doi: 10.1016/j.optmat.2019.01.037
39. [39]
  J. Song, K. Zhao, H. Zhang, C.K. Wang, Mol. Phys. 117 (2018) 672–680. doi: 10.1002/gps.4798
40. [40]
  V.A. Galievsky, S.I. Druzhinin, A. Demeter, et al., ChemPhysChem 6 (2005) 2307–2323. doi: 10.1002/cphc.200500267
41. [41]
  J. Lei, C. Guo, F. Liu, et al., Dye. Pigment. 170 (2019) 107607. doi: 10.1016/j.dyepig.2019.107607
42. [42]
  E. Ripaud, C. Mallet, M. Allain, et al.; Tetrahedron Lett. 52 (2011) 6573–6577. doi: 10.1016/j.tetlet.2011.09.129
43. [43]
  H. Umezawa, S. Okada, H. Oikawa, H. Matsuda, H. Nakanishi, Bull. Chem. Soc. Jpn. 80 (2007) 1413–1417. doi: 10.1246/bcsj.80.1413
44. [44]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel HB, et al., Gaussian 16, Revision A. 03. Wallingford CT: Gaussian, Inc. 2016.
45. [45]
  Y. Yuan, W. Zhou, M. Tian, et al., Dye. Pigment. 188 (2021) 109235. doi: 10.1016/j.dyepig.2021.109235
46. [46]
  Q. Li, W. Perrie, Z. Li, S.P. Edwardson, G. Dearden, Opto-Electron. Adv. 5 (2022) 210036. doi: 10.29026/oea.2022.210036
47. [47]
  K. Wang, H. Long, M. Fu, G. Yang, P.X. Lu, Opt. Lett. 35 (2010) 1560–1562. doi: 10.1364/OL.35.001560
48. [48]
  V. Ramar, K. Balasubramanian, Appl. Phys. A 124 (2018) 779. doi: 10.1007/s00339-018-2191-3
49. [49]
  G.Y. Zhou, X.M. Wang, D. Wang, et al., Opt. Commun. 190 (2001) 345–349. doi: 10.1016/S0030-4018(01)01058-6
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