Citation: Ming-jian Jiang, Xin-yuan Li, Lei-tao Sun, Xiao-long Niu, Qiu-min Liang, Xiao-qiang Cai, Jin-chang Huang, Jun Ling, Yue-qi Mo. Special Photophysical Properties of Poly(2, 11-diquinoxalinopyrene)s[J]. Chinese Journal of Polymer Science, ;2017, 35(9): 1097-1109. doi: 10.1007/s10118-017-1961-2 shu

Special Photophysical Properties of Poly(2, 11-diquinoxalinopyrene)s

a.
College of Materials Science and Engineering, South China University of Technology, Guangzhou 510640, China
b.
Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China

Corresponding author: Jun Ling, lingjun@zju.edu.cn Yue-qi Mo, pomoy@scut.edu.cn
Received Date: 26 February 2017
Revised Date: 14 April 2017
Accepted Date: 17 April 2017

Fund Project: the National Natural Science Foundation of China 21174042Fund of Project on the Integration of Industry, Education and Research of Guangdong Province 2013B090500072

A diquinoxalinopyrene (DQP) derivative and the corresponding oligomers (PDQPs) with M_n of ca. 3300, 4200, 5600, and 7300 have been synthesized. It is found that the band gaps and highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO) levels between DQP and its homopolymers only have a slight difference, implying a limited conjugation extension achieved from unimer to heptamer. The DFT calculation is in accordance with the experimental results. It reveals that the nodal planes are across the 2, 11-positions in the LUMO and/or HOMO of DQP, dimer and trimer, which can be used to explain this special phenomenon.
- Polydiquinoxalinopyrene,
- Photophysical properties,
- Nodal
1. [1]
  Lin, Y.Y., Gundlach, D.J., Nelson, S.F. and Jackson, T.N., IEEE Electr. Device L., 1997, 18(12): 606 doi: 10.1109/55.644085
2. [2]
  Klauk, H., Zschieschang, U., Pflaum, J. and Halik, M., Nature, 2007, 445(7129): 745 doi: 10.1038/nature05533
3. [3]
  Heringdorf, F., Reuter, M.C. and Tromp, R.M., Nature, 2001, 412(6846): 517 doi: 10.1038/35087532
4. [4]
  Halik, M., Klauk, H., Zschieschang, U., Schmid, G., Dehm, C., Schutz, M., Maisch, S., Effenberger, F., Brunnbauer, M. and Stellacci, F., Nature, 2004, 431(7011): 963 doi: 10.1038/nature02987
5. [5]
  Giri, G., Verploegen, E., Mannsfeld, S.C.B., Atahan-Evrenk, S., Kim, D.H., Lee, S.Y., Becerril, H.A., Aspuru-Guzik, A., Toney, M.F. and Bao, Z., Nature, 2011, 480(7378): 504 doi: 10.1038/nature10683
6. [6]
  Yazyev, O.V., Acc. Chem. Res., 2013, 46(10): 2319 doi: 10.1021/ar3001487
7. [7]
  Cai, J., Ruffieux, P., Jaafar, R., Bieri, M., Braun, T., Blankenburg, S., Muoth, M., Seitsonen, A.P., Saleh, M., Feng, X., Muellen, K. and Fasel, R., Nature, 2010, 466(7305): 470 doi: 10.1038/nature09211
8. [8]
  Kosynkin, D.V., Higginbotham, A.L., Sinitskii, A., Lomeda, J.R., Dimiev, A., Price, B.K. and Tour, J.M., Nature, 2009, 458(7240): 872 doi: 10.1038/nature07872
9. [9]
  Magda, G.Z., Jin, X., Hagymasi, I., Vancso, P., Osvath, Z., Nemes-Incze, P., Hwang, C., Biro, L.P. and Tapaszto, L., Nature, 2014, 514(7524): 608 doi: 10.1038/nature13831
10. [10]
  Son, Y.W., Cohen, M.L. and Louie, S.G., Nature, 2006, 444(7117): 347 doi: 10.1038/nature05180
11. [11]
  Li, J.B. and Zhang, Q.C., ACS Appl. Mater. Interfaces, 2015, 7(51): 28049 doi: 10.1021/acsami.5b00113
12. [12]
  Li, J.B., Chen, S., Wang, Z.L. and Zhang, Q.C., Chem. Rec., 2016, 16(3): 1518 doi: 10.1002/tcr.201600015
13. [13]
  Wang, C.Y., Gu, P.Y., Hua, B.L. and Zhang, Q.C., J. Mater. Chem. C, 2015, 3(39): 10055 doi: 10.1039/C5TC02080H
14. [14]
  Henning, S., Adv. Mater., 2014, 26(9): 1319 doi: 10.1002/adma.201304346
15. [15]
  Chen, W.Q. and Zhang, Q.C., J. Mater. Chem. C, 2017, 5(6): 1275 doi: 10.1039/C6TC05066B
16. [16]
  Stille, J.K. and Mainen, E.L., J. Polym. Sci. Polym. Phys., 1966, 4(4): 665
17. [17]
  Stille, J.K. and Mainen, E.L., Macromolecules, 1968, 1(1): 36 doi: 10.1021/ma60001a007
18. [18]
  Imai, K., Kuhihara, M., Mathias, L., Wittmann, J., Alston, W.B. and Stille, J.K., Macromolecules, 1973, 6(2): 158 doi: 10.1021/ma60032a002
19. [19]
  Gao, B., Wang, M., Cheng, Y., Wang, L., Jing, X. and Wang, F., J. Am. Chem. Soc., 2008, 130(26): 8297 doi: 10.1021/ja800311a
20. [20]
  Mateo-Alonso, A., Chem. Soc. Rev., 2014, 43(17): 6311 doi: 10.1039/C4CS00119B
21. [21]
  Wang, C.Y., Zhang, J., Long, G.K., Naoki, A., Hiroko, Y., Zhao, Y. and Zhang, Q.C., Angew. Chem. Int. Ed., 2015, 54(21): 6292 doi: 10.1002/anie.201500972
22. [22]
  Wu, J.S., Rui, X.H., Long, G.K., Chen, W.Q., Yan, Q.Y. and Zhang, Q.C., Angew. Chem. Int. Ed., 2015, 54(25): 7354 doi: 10.1002/anie.v54.25
23. [23]
  Zhang, J., Wang, C.Y., Long, G.K., Naoki, A., Hiroko, Y. and Zhang, Q.C., Chem. Sci., 2016, 7(2): 1309 doi: 10.1039/C5SC03604F
24. [24]
  McGrath, K.K., Jang, K., Robins, K.A. and Lee, D.C., Chem. Eur. J., 2009, 15(16): 4070 doi: 10.1002/chem.v15:16
25. [25]
  Moustafa, R.M., Degheili, J.A., Patra, D. and Kaafarani, B.R., J. Phys. Chem. A, 2009, 113(7): 1235 doi: 10.1021/jp809830x
26. [26]
  Chen, S., Read, F.S., Ahmida, M., Kaafarani, B.R. and Eichhorn, S.H., Org. Lett., 2013, 15(3): 558 doi: 10.1021/ol303375x
27. [27]
  Kohl, B., Rominger, F. and Mastalerz, M., Org. Lett., 2014, 16(3): 704 doi: 10.1021/ol403383y
28. [28]
  Kohl, B., Rominger, F. and Mastalerz, M., Angew. Chem. Int. Ed., 2015, 54(20): 6051 doi: 10.1002/anie.201411972
29. [29]
  More, S., Bhosale, R. and Mateo-Alonso, A., Chem. Eur. J., 2014, 20(34): 10626 doi: 10.1002/chem.v20.34
30. [30]
  Luo, M., Shadnia, H., Qian, G., Du, X., Yu, D., Ma, D., Wright, J.S. and Wang, Z.Y., Chem. Eur. J., 2009, 15(35): 8902 doi: 10.1002/chem.v15:35
31. [31]
  Shao, J., Chang, J. and Chi, C., Org. Biomol. Chem., 2012, 10(35): 7045 doi: 10.1039/c2ob25680k
32. [32]
  Kulisic, N., More, S. and Mateo-Alonso, A., Chem. Commun., 2011, 47(1): 514 doi: 10.1039/C0CC02249G
33. [33]
  More, S., Choudhary, S., Higelin, A., Krossing, I., Melle-Franco, M. and Mateo-Alonso, A., Chem. Commun., 2014, 50(16): 1976 doi: 10.1039/c3cc48742c
34. [34]
  More, S., Bhosale, R., Choudhary, S. and Mateo-Alonso, A., Org. Lett., 2012, 14(16): 4170 doi: 10.1021/ol301841h
35. [35]
  Wang, Z.L., Miao, J.W., Long, G.K., Gu, P.Y., Li, J.B., Naoki, A., Hiroko, Y., Liu, Bi. and Zhang, Q.C., Chem. Asian J., 2016, 11(4): 482 doi: 10.1002/asia.v11.4
36. [36]
  Lee, D.C., Jang, K., McGrath, K.K., Uy, R., Robins, K.A. and Hatchett, D.W., Chem. Mater., 2008, 20(11): 3688 doi: 10.1021/cm800521p
37. [37]
  Jang, K., Kinyanjui, J.M., Hatchett, D.W. and Lee, D.C., Chem. Mater., 2009, 21(10): 2070 doi: 10.1021/cm8029455
38. [38]
  Jang, K., Ranasinghe, A.D., Heske, C. and Lee, D.C., Langmuir, 2010, 26(16): 13630 doi: 10.1021/la101921c
39. [39]
  Feng, X., Hu, J.Y., Tomiyasu, H., Tao, Z., Redshaw, C., Elsegood, M.R.J., Horsburgh, L., Teat, S.J., Wei, X.F. and Yamato, T., RSC Adv., 2015, 5(12): 8835 doi: 10.1039/C4RA12216J
40. [40]
  Wang, M., Li, Y., Xie, Z. and Wang, L., Sci. China. Chem., 2011, 54(4): 656 doi: 10.1007/s11426-011-4238-6
41. [41]
  Hu, J., Zhang, D. and Harris, F.W., J. Org. Chem., 2005, 70(2): 707 doi: 10.1021/jo048509q
42. [42]
  Wang, N., Bao, X.C., Yan, Y., Ouyang, D., Sun, M.L., Roy, V.A.L., Lee, C.S. and Yang, R.Q., J. Polym. Sci., Part A: Polym. Chem., 2014, 52(22): 3198 doi: 10.1002/pola.v52.22
43. [43]
  Kawano, S.I., Baumgarten, M., Chercka, D., Enkelmann, V. and Muellen, K., Chem. Commun., 2013, 49(44): 5058 doi: 10.1039/c3cc39141h
44. [44]
  Jin, G., Xia, L., Liu, Z., Lin, H., Ling, J., Wu, H., Hou, L. and Mo, Y., J. Mater. Chem. C, 2016, 4(5): 905 doi: 10.1039/C5TC03665H
45. [45]
  Yamamoto, T., Morita. A., Miyazaki, Y., Maruyama, T., Wakayama, H., Zhou, Z.H., Nakamura, Y., Kanbara, T., Sasaki, S. and Kubota, K., Macromolecules, 1992, 25(4): 1214 doi: 10.1021/ma00030a003
46. [46]
  Wang, J., Zhang, C.Q., Zhong, C.M., Hu, S.J., Chang, X.Y., Mo, Y.Q., Chen, X. and Wu, H.B., Macromolecules, 2011, 44(1): 17 doi: 10.1021/ma102446b
47. [47]
  Jiang, L., Papageorgiou, A.C., Oh, S.C., Saglam, O., Reichert, J., Duncan, D.A., Zhang, Y.Q., Klappenberger, F., Guo, Y., Allegretti, F., More, S., Bhosale, R., Mateo-Alonso, A. and Barth, J.V., ACS Nano, 2016, 10(1): 1033 doi: 10.1021/acsnano.5b06340
48. [48]
  Jiang, M.J., Xiao, W.J., Huang, J.C., Li, W.S. and Mo, Y.Q., Tetrahedron, 2016, 72(7): 979 doi: 10.1016/j.tet.2015.12.069
49. [49]
  Huang, J., Xiao, B., Wang, J., Wang, Y., Peng, X., Miao, X., Pan, Q., Mo, Y., Deng, W., Wu, H. and Cao, Y., Org. Lett., 2014, 15(10): 2311
50. [50]
  Qiao, Y., Zhang, J., Xu, W. and Zhu, D., Tetrahedron, 2011, 67(19): 3395 doi: 10.1016/j.tet.2011.03.055
51. [51]
  Zhan, X.J., Zhang, J., Tang, S., Lin, Y.X., Zhao, M., Yang, J., Zhang, H.L., Peng, Q., Yu, G. and Li, Z., Chem. Commun., 2015, 51(33): 7156 doi: 10.1039/C5CC00966A
52. [52]
  Okamoto, A., Kanatani, K. and Saito, I., J. Am. Chem. Soc., 2004, 126(15): 4820 doi: 10.1021/ja039625y
53. [53]
  Maeda, H., Maeda, T., Mizuno, K., Fujimoto, K., Shimizu, H. and Inouye, M., Chem. Eur. J., 2006, 12(3): 824 doi: 10.1002/(ISSN)1521-3765
54. [54]
  Yang, C., Scheiber, H., List, E.J.W., Jacob, J. and Muellen, K., Macromolecules, 2006, 39(16): 5213 doi: 10.1021/ma061007p
55. [55]
  Zhou, W.Q., Peng, H.P., Xu, J.K., Xia, H.Y. and Pu, S.Z., Polym. Int., 2008, 57(1): 92 doi: 10.1002/(ISSN)1097-0126
56. [56]
  Kawano, S.I., Yang, C., Ribas, M., Baluschev, S., Baumgarten, M. and Muellen, K., Macromolecules, 2008, 41(21): 7933 doi: 10.1021/ma8017316
57. [57]
  Bredas, J.L., Silbey, R., Boudreaux, D.S. and Chance, R.R., J. Am. Chem. Soc., 1983, 105(22): 6555 doi: 10.1021/ja00360a004
58. [58]
  Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., and et al., Gaussian 03. Wallingford CT: Gaussian Inc. 2004.
59. [59]
  Liu, J. and Ling, J., J. Phys. Chem. A, 2015, 119(27): 7070 doi: 10.1021/acs.jpca.5b04654
60. [60]
  Ling, J. and Huang, Y., Macromol. Chem. Phys., 2010, 211(15): 1708 doi: 10.1002/macp.201000115
61. [61]
  Ling, J., Shen, J. and Hogen-Esch, T.E., Polymer, 2009, 50(15): 3575 doi: 10.1016/j.polymer.2009.06.006
62. [62]
  Cao, F., Yuan, Z., Liu, J. and Ling, J., RSC Adv., 2015, 5(124): 102535 doi: 10.1039/C5RA19710D
63. [63]
  He, Y.Q. and Zhong, Y.W., Chem. Commun., 2015, 51(16): 3411 doi: 10.1039/C4CC09480H
64. [64]
  Ottonelli, M., Piccardo, M., Duce, D., Thea, S. and Dellepiane, G., J. Phys. Chem. A, 2012, 116(1): 611 doi: 10.1021/jp2084764
65. [65]
  Sriwichitkamol, K., Suramitr, S., Poolmee, P. and Hannongbua, S., J. Theor. Comput. Che., 2006, 5(3): 595 doi: 10.1142/S0219633606002520
66. [66]
  Kreyenschmidt, M., Baumgarten, M., Tyutyulkov, N. and Mullen, K., Angew. Chem. Int. Ed., 1994, 33(19): 1957 doi: 10.1002/(ISSN)1521-3773
1. [1]
  Zhiyuan Chen , Jinyu Song , Lai Hu , Peng Xu , Zhengyi Sun , Xiao-Chun Hang , Hongjun Zhu , Senqiang Zhu , Rui Liu . Structure-aware machine learning for predicting photophysical properties of MR-TADF materials. Chinese Chemical Letters, 2026, 37(7): 111967-. doi: 10.1016/j.cclet.2025.111967
2. [2]
  Shengwen Guan , Zhaotong Wei , Ningxu Han , Yude Wei , Bin Xu , Ming Wang , Junjuan Shi . Construction of metallo-complexes with 2,2′:6′,2″-terpyridine substituted triphenylamine in different modified positions and their photophysical properties. Chinese Chemical Letters, 2024, 35(7): 109348-. doi: 10.1016/j.cclet.2023.109348
3. [3]
  Jiaxiang Guo , Zeyi Li , Tianyu Zhang , Xinyu Tian , Yue Wang , Chuandong Dou . Thienothiophene-centered ladder-type π-systems that feature distinct quinoidal π-extension. Chinese Chemical Letters, 2024, 35(5): 109337-. doi: 10.1016/j.cclet.2023.109337
4. [4]
  Youxiang He , Yongfa Zhu , Ming Luo , Haiping Xia . A nonalternant analogue of pentacene incorporating a non-terminal azulene unit. Chinese Chemical Letters, 2025, 36(7): 110463-. doi: 10.1016/j.cclet.2024.110463
5. [5]
  Zijian Zhang , Fangxin Du , Lijia Liu , Yixiang Sun , Jie Xue , Hanshen Xin . 1-Azaazulene constructs: Overcoming the weak fluorescence of azulene derivatives via S₁-S₀ transitions. Chinese Chemical Letters, 2026, 37(6): 111987-. doi: 10.1016/j.cclet.2025.111987
6. [6]
  Xiulian Cai , Qilin Wei , Yaping Gong , Tong Chang , Tongtong Kou , Ziyang Song , Zengshan Yue , Huanxin Su , Yuanxiang You , Chengmin Ji , Xinxin Han , Shiguo Han , William W. Yu . Enhanced luminescence efficiency and stability in Mn-based organic-inorganic hybrid metal halides via chlorination effect. Chinese Chemical Letters, 2026, 37(9): 111515-. doi: 10.1016/j.cclet.2025.111515
7. [7]
  Xiaoyu Chen , Jiahao Hu , Jingyi Lin , Haiyang Huang , Changqing Ye , Hongli Bao . Biisoindolylidene solvatochromic fluorophores: Synthesis and photophysical properties. Chinese Chemical Letters, 2025, 36(2): 109923-. doi: 10.1016/j.cclet.2024.109923
8. [8]
  Shuqi Chen , Cankun Zhang , Xiaonuo Dong , Hui-Jun Zhang , Jianbin Lin . Synthesis and photophysical properties of alternating donor-acceptor conjugated nanorings. Chinese Chemical Letters, 2025, 36(6): 110354-. doi: 10.1016/j.cclet.2024.110354
9. [9]
  Jianmin Jiao , Jiehao Yu , Xueqi Tian , Xiao-Yu Hu . TPE-embedded functional macrocycles: From structural design to photophysical property and application. Chinese Chemical Letters, 2025, 36(6): 111026-. doi: 10.1016/j.cclet.2025.111026
10. [10]
  Qianwei Liu , Xinhong Xiong , Numan Ahmed , Peisong Tang , Jiaxi Cui . Crystal hydrogels: Strategies, properties, and applications. Chinese Chemical Letters, 2026, 37(5): 111707-. doi: 10.1016/j.cclet.2025.111707
11. [11]
  Bowen Song , Chenxu Shi , Yinghao Qu , Hongjun Liu , Hui Yang , Xiaoming Wu , Xijun Liu . The electrical properties and charge transport mechanism of MXenes. Chinese Chemical Letters, 2025, 36(6): 110823-. doi: 10.1016/j.cclet.2025.110823
12. [12]
  Zhaoyu Yan , Yuanhao Feng , Zhewen Ma , Wei Zheng . Chiroptical properties and supramolecular chirality transfer in a bilayer spironanographene. Chinese Chemical Letters, 2026, 37(10): 112890-. doi: 10.1016/j.cclet.2026.112890
13. [13]
  Zhihao Gu , Jiabo Le , Hehe Wei , Zehui Sun , Mahmoud Elsayed Hafez , Wei Ma . Unveiling the intrinsic properties of single NiZnFeO_x entity for promoting electrocatalytic oxygen evolution. Chinese Chemical Letters, 2024, 35(4): 108849-. doi: 10.1016/j.cclet.2023.108849
14. [14]
  Wenzhong Zhang , Zirui Yan , Lingcheng Chen , Yi Xiao . Sn-fused perylene diimides: Synthesis, mechanism, and properties. Chinese Chemical Letters, 2024, 35(10): 109582-. doi: 10.1016/j.cclet.2024.109582
15. [15]
  Rongjian Chen , Jiahui Liu , Caixia Lin , Yuanming Li , Yanhou Geng , Yaofeng Yuan . Synthesis and properties of tetraphenylethene cationic cyclophanes based on o-carborane skeleton. Chinese Chemical Letters, 2024, 35(12): 110074-. doi: 10.1016/j.cclet.2024.110074
16. [16]
  Xinyu Liu , Jialin Yang , Zonglin He , Jiaoyan Ai , Lina Song , Baohua Liu . Linear polyurethanes with excellent comprehensive properties from poly(ethylene carbonate) diol. Chinese Chemical Letters, 2025, 36(1): 110236-. doi: 10.1016/j.cclet.2024.110236
17. [17]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
18. [18]
  Ke-Lin Zhu , Zhi-Ao Li , Jiaqi Liang , Yong He , Han-Yuan Gong . Atropisomeric carbon-rich macrocycles: Synthesis, structural evolution, and properties. Chinese Chemical Letters, 2026, 37(2): 111629-. doi: 10.1016/j.cclet.2025.111629
19. [19]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
20. [20]
  Yanbing Shen , Yuan Yuan , Yaxin Wang , Xiaonan Ma , Wensheng Yang , Yulan Chen . Dihydroanthracene bridged bis-naphthopyrans: A multimodal chromophore with mechano- and photo-chromic properties. Chinese Chemical Letters, 2024, 35(5): 108949-. doi: 10.1016/j.cclet.2023.108949

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2169)
HTML views(55)

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