Citation: Lun-jun Qu, Li-shuang Tang, Si-wei Liu, Zhen-guo Chi, Xu-dong Chen, Yi Zhang, Jia-rui Xu. Preparation and Photoluminescent Properties of Polyimides Containing Triphenylamine Pendant Group[J]. Acta Polymerica Sinica, ;2018, 0(11): 1430-1441. doi: 10.11777/j.issn1000-3304.2018.18075 shu

Preparation and Photoluminescent Properties of Polyimides Containing Triphenylamine Pendant Group

PCFM Lab, GD HPPC Lab, Guangdong Engineering Technology Research Center for High-performance Organic and Polymer Photoelectric Functional Films, School of Chemistry, Sun Yat-sen University, Guangzhou 510275

Corresponding author: Yi Zhang, ceszy@mail.sysu.edu.cn
Received Date: 7 March 2018
Available Online: 1 August 2018

Two triphenylamines (TPA) based diamine monomers, TPCDA and TPNDA, were successfully designed and synthesized, which were of similar chemical structures but different electronic effects. Both TPCDA and TPNDA exhibit aggregation induced emission (AIE) phenomenon, and show intense emission at 395 and 447 nm in the solid state, respectively. They were polymerized with two dianhydrides (BPADA and HQDPA), respectively, to form four novel polyimides with excellent thermal stability. The fluorescence of the polyimides derived from TPNDA, TPNBPI and TPNHPI, is totally quenched. However, for the TPCDA-based polyimides, TPCBPI and TPCHPI show bright orange photoluminescence at 565 and 585 nm in their films, respectively. By increasing the concentration of TPCBPI and TPNBPI in N-methyl pyrrolidone (NMP) solution, their emission changes from non-luminescence to bright blue emission, followed by a red-shift due to the formation of strong intermolecular charge transfer, and they show green emission at 504 nm and 508 nm at the concentration of 4 mg·mL⁻¹. The photoluminescence of TPCDA-based polyimides is similar to the composite system, where TPA is doped in a polyimide with the same main-chain structure. However, the theoretical calculations for the model units of the resulting polyimides show that both the conjugated TPNDA-based system and the unconjugated TPCDA-based system are non-luminescent due to an inhibited transition from HOMO to LUMO level. Further studies show that the luminescent properties of the TPCDA-based polyimides are owing to the following two reasons: (1) Compared with the TPNDA-based system, the sp³ hybridized carbon atom in the TPCDA-based system separates the TPA structure from the polyimide main chain, which dispels the influence of the intramolecular charge transfer effect of the polyimide on TPA; (2) The relatively independent TPA moieties can have strong intermolecular charge transfer interaction with the polyimide main chains, which leads this system to exhibiting a strong orange fluorescence with a 184 nm red-shift of the max emission wavelength. This work demonstrates a simple strategy to develop aromatic polyimides with high fluorescence for potential applications in organic photoelectric field.
- Polyimide,
- Triphenylamine,
- Photoluminescence,
- Intramolecular CTC,
- Intermolecular CTC
1. [1]
  Kuik M, Wetzelaer G J A H, Nicolai H T, Craciun N I, de Leeuw D M, Blom P W M. Adv Mater, 2014, 26(4): 512 − 531
2. [2]
  Guan X, Zhang K, Huang F, Bazan G C, Cao Y. Adv Funct Mater, 2012, 22(13): 2846 − 2854
3. [3]
  Ellmer K. Nat Photon, 2012, 6(12): 808 − 816
4. [4]
  Kim F S, Ren G Q, Jenekhe S A. Chem Mater, 2011, 23(3): 682 − 732
5. [5]
  Yu L, Liu J, Hu S J, He R F, Yang W, Wu H B, Peng J B, Xia R D, Bradley D D C. Adv Funct Mater, 2013, 23(35): 4366 − 4376
6. [6]
  Mazzio K A, Luscombe C K. Chem Soc Rev, 2015, 44(1): 78 − 90
7. [7]
  Gao X K, Hu Y B. J Mater Chem C, 2014, 2(17): 3099 − 3117
8. [8]
  Liaw D J, Wang K L, Huang Y C, Lee K R, Lai J Y, Ha C S. Prog Polym Sci, 2012, 37(7): 907 − 974
9. [9]
  Feng L H, Chen Z B. Polymer, 2005, 46(11): 3952 − 3956
10. [10]
  Mal'tsev E I, Brusentseva M A, Lypenko D A, Berendyaev V I, Kolesnikov V A, Kotov B V, Vannikov A V. Polym Adv Technol, 2000, 11(7): 325 − 329
11. [11]
  Ng W Y, Gong X, Chan W K. Chem Mater, 1999, 11(4): 1165 − 1170
12. [12]
  Hsu S C, Whang W T, Chao C S. Thin Solid Films, 2007, 515(17): 6943 − 6948
13. [13]
  Yang Tingting(杨婷婷), Zhou Zhuxin(周竹欣), Zhang Yi(张艺), Liu Siwei(刘四委), Chi Zhenguo(池振国), Xu Jiarui(许家瑞). Acta Polymprica Sinica(高分子学报), 2017, (3): 411-428
14. [14]
  Yen H J, Chen C J, Liou G S. Adv Funct Mater, 2013, 23(42): 5307 − 5316
15. [15]
  Kanosue K, Shimosaka T, Wakita J, Ando S. Macromolecules, 2015, 48(6): 1777 − 1785
16. [16]
  Thelakkat M, Posch P, Schmidt H W. Macromolecules, 2001, 34(21): 7441 − 7447
17. [17]
  Wu J H, Liou G S. Polym Chem, 2015, 6(29): 5225 − 5232
18. [18]
  Yen H J, Chen C J, Liou G S. Chem Commun, 2013, 49(6): 630 − 632
19. [19]
  Zhou Z X, Zhang Y, Liu S W, Chi Z G, Chen X D, Xu J R. J Mater Chem C, 2016, 4(44): 10509 − 10517
20. [20]
  Zhou Z X, Huang W X, Long Y B, Chen Y Q, Yu Q X, Zhang Y, Liu S W, Chi Z G, Chen X D, Xu J R. J Mater Chem C, 2017, 5(33): 8545 − 8552
21. [21]
  Qu L J, Huang S D, Zhang Y, Chi Z G, Liu S W, Chen X D, Xu J R. J Mater Chem C, 2017, 5(26): 6457 − 6466
22. [22]
  Qu L J, Tang L S, Bei R X, Zhao J, Chi Z G, Liu S W, Chen X D, Aldred M P, Zhang Y, Xu J R. ACS Appl Mater Interfaces, 2018, 10(14): 11430 − 11435
23. [23]
  Eastmond G C, Paprotny J, Pethrick R A, Santamaria-Mendia F. Macromolecules, 2006, 39(22): 7534 − 7548
24. [24]
  Cheng S H, Hsiao S H, Su T H, Liou G S. Macromolecules, 2005, 38(2): 307 − 316
25. [25]
  Luo J D, Xie Z L, Lam J W Y, Cheng L, Chen H Y, Qiu C F, Kwok H S, Zhan X W, Liu Y Q, Zhu D B, Tang B Z. Chem Commun, 2001, 18(18): 1740 − 1741
26. [26]
  Hong Y N, Lam J W Y, Tang B Z. Chem Commun, 2009, 40(45): 4332 − 4353
27. [27]
  Mei J, Leung N L C, Kwok R T K, Lam J W Y, Tang B Z. Chem Rev, 2015, 115(21): 11718 − 11940
28. [28]
  Liang Z Q, Wang X M, Dai G L, Ye C Q, Zhou Y Y, Tao X T. New J Chem, 2015, 39(11): 8874 − 8880
29. [29]
  Tian G J, Huang W, Cai S Y, Zhou H T, Li B, Wang Q C, Su J H. RSC Adv, 2014, 4(73): 38939 − 38942
30. [30]
  Song Q B, Chen K, Sun J W, Wang Y S, Ouyang M, Zhang C. Tetrahedron Lett, 2014, 55(20): 3200 − 3205
31. [31]
  Liaw D J, Wang K L, Huang Y C, Lee K R, Lai J Y, Ha C S. Prog Polym Sci, 2012, 37(7): 907 − 974
32. [32]
  Wakita J, Sekino H, Sakai K, Urano Y, Ando S. J Phys Chem B, 2009, 113(46): 15212 − 15224
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