Citation: Bo Yu, Pengchen Du, Jianwen Guo, Hanshen Xin, Jianhua Zhang. Nonalternant isomer of pentacene fusing two azulene units[J]. Chinese Chemical Letters, ;2024, 35(5): 109321. doi: 10.1016/j.cclet.2023.109321 shu

Nonalternant isomer of pentacene fusing two azulene units

Bo Yu ^{a, b} ,
Pengchen Du ^b ,
Jianwen Guo ^b ,
Hanshen Xin ^{a, b, *,} ,
Jianhua Zhang ^{a, b, *,}

a.
Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444, China
b.
School of Microelectronics, Shanghai University, Shanghai 201800, China

xinhanshen@shu.edu.cn

jhzhang@oa.shu.edu.cn

Received Date: 7 September 2023
Revised Date: 14 November 2023
Accepted Date: 17 November 2023
Available Online: 19 November 2023

Figures(6)

Azulene is a promising building block for creating innovative polycyclic aromatic hydrocarbons. This study involved the construction of three nonalternant isomers of pentacene by fusing two azulene units, named Az-PH1/2/3. Az-PH1 was initially developed through the rhodium(II)-catalyzed cyclization of bis(N-tosylhydrazone)s. Intriguingly, Az-PH1 was also unexpectedly obtained during a nickel(0)-catalyzed one-step tandem reaction. We investigated the optical and electrochemical properties, aromaticity, and photo-oxidative stability of Az-PH1, comparing it with the well-known pentacene using density functional theory, electrochemical, and photophysical tests. Our results showed that the azulene-fusing strategy resulted in a molecule with narrow optical bandgaps (2.046 eV) and a long half-life time under ambient air conditions.
- Azulene,
- Isomer,
- Polycyclic aromatic hydrocarbon,
- Nickel(0)-catalyzed,
- Photo-oxidative stability
1. [1]
  A. Pron, P. Gawrys, M. Zagorska, et al., Chem. Soc. Rev. 39 (2010) 2577–2632. doi: 10.1039/b907999h
2. [2]
  K. Takimiya, S. Shinamura, I. Osaka, et al., Adv. Mater. 23 (2011) 4347–4370. doi: 10.1002/adma.201102007
3. [3]
  J. Mei, Y. Diao, A.L. Appleton, et al., J. Am. Chem. Soc. 135 (2013) 6724–6746. doi: 10.1021/ja400881n
4. [4]
  B. Hou, J. Li, X. Yang, et al., Chin. Chem. Lett. 33 (2022) 2147–2150. doi: 10.1016/j.cclet.2021.08.079
5. [5]
  T. Yang, Q. Wu, F. Dai, et al., Adv. Funct. Mater. 30 (2019) 1903889.
6. [6]
  H. Jiang, S. Zhu, Z. Cui, et al., Chem. Soc. Rev. 51 (2022) 3071. doi: 10.1039/D1CS01136G
7. [7]
  C. Sutton, C. Risko, J.L. Brédas, Chem. Mater. 28 (2015) 3–16.
8. [8]
  T.G. Lohr, J.I. Urgel, K. Eimre, et al., J. Am. Chem. Soc. 142 (2020) 13565–13572. doi: 10.1021/jacs.0c05668
9. [9]
  P.M. Ajayan, Nature 575 (2019) 49–50.
10. [10]
  K.S. Novoselov, V.I. Fal'ko, L. Colombo, et al., Nature 490 (2012) 192–200. doi: 10.1038/nature11458
11. [11]
  X. Li, X. Wang, L. Zhang, et al., Science 319 (2008) 1229–1232. doi: 10.1126/science.1150878
12. [12]
  R. Dorel, A.M. Echavarren, Acc. Chem. Res. 52 (2019) 1812–1823. doi: 10.1021/acs.accounts.9b00227
13. [13]
  H. Okamoto, N. Kawasaki, Y. Kaji, et al., J. Am. Chem. Soc. 130 (2008) 10470–10471. doi: 10.1021/ja803291a
14. [14]
  C. Tonshoff, H.F. Bettinger, Chemistry 27 (2021) 3193–3212. doi: 10.1002/chem.202003112
15. [15]
  J.I. Urgel, S. Mishra, H. Hayashi, et al., Nat. Commun. 10 (2019) 861. doi: 10.1038/s41467-019-08650-y
16. [16]
  H. Xin, C. Ge, X. Jiao, et al., Angew. Chem. Int. Ed. 57 (2018) 1322–1326. doi: 10.1002/anie.201711802
17. [17]
  S. Wang, M. Tang, L. Wu, et al., Angew. Chem. Int. Ed. 61 (2022) e202205658. doi: 10.1002/anie.202205658
18. [18]
  J.X. Dong, H.L. Zhang, Chin. Chem. Lett. 27 (2016) 1097–1104. doi: 10.1016/j.cclet.2016.05.005
19. [19]
  P. Liu, X.Y. Chen, J. Cao, et al., J. Am. Chem. Soc. 143 (2021) 5314–5318. doi: 10.1021/jacs.1c01826
20. [20]
  L. Ou, Y. Zhou, B. Wu, et al., Chin. Chem. Lett. 30 (2019) 1903–1907. doi: 10.1016/j.cclet.2019.08.015
21. [21]
  D.L. Wang, S.F. Li, W. Li, et al., Chin. Chem. Lett. 22 (2011) 789–792. doi: 10.1016/j.cclet.2011.01.003
22. [22]
  H. Xin, B. Hou, X. Gao, Acc. Chem. Res. 54 (2021) 1737–1753. doi: 10.1021/acs.accounts.0c00893
23. [23]
  Y. Wang, Z. Jiang, L. Liao, Chin. Chem. Lett. 27 (2016) 1293–1303. doi: 10.1016/j.cclet.2016.07.004
24. [24]
  F. Ullah, H. Chen, C.Z. Li, Chin. Chem. Lett. 28 (2017) 503–511. doi: 10.1016/j.cclet.2016.11.009
25. [25]
  L.C. Murfin, M. Weber, S.J. Park, et al., J. Am. Chem. Soc. 141 (2019) 19389–19396. doi: 10.1021/jacs.9b09813
26. [26]
  H. Nishimura, N. Ishida, A. Shimazaki, et al., J. Am. Chem. Soc. 137 (2015) 15656–15659. doi: 10.1021/jacs.5b11008
27. [27]
  X. Zhang, T. Li, Chin. Chem. Lett. 28 (2017) 2058–2064. doi: 10.1016/j.cclet.2017.09.008
28. [28]
  Y. Fei, J. Liu, Adv. Sci. 9 (2022) e2201000. doi: 10.1002/advs.202201000
29. [29]
  H. Luo, J. Liu, Angew. Chem. Int. Ed. 62 (2023) e202302761. doi: 10.1002/anie.202302761
30. [30]
  Y. Liang, S. Wang, M. Tang, et al., Angew. Chem. Int. Ed. 62 (2023) e202218839. doi: 10.1002/anie.202218839
31. [31]
  K. Wang, L. Chen, Y.Y. Huang, et al., Chin. J. Chem. 41 (2023) 2589–2596. doi: 10.1002/cjoc.202300149
32. [32]
  M. Murai, S. Iba, H. Ota, et al., Org. Lett. 19 (2017) 5585–5588. doi: 10.1021/acs.orglett.7b02729
33. [33]
  A. Ong, T. Tao, Q. Jiang, et al., Angew. Chem. Int. Ed. 61 (2022) e202209286. doi: 10.1002/anie.202209286
34. [34]
  H. Xin, J. Li, R.Q. Lu, et al., J. Am. Chem. Soc. 142 (2020) 13598–13605. doi: 10.1021/jacs.0c06299
35. [35]
  Y. Shibuya, K. Aonuma, T. Kimura, et al., J. Phys. Chem. C 124 (2020) 4738–4746. doi: 10.1021/acs.jpcc.9b11214
36. [36]
  Y. Xia, Z. Liu, Q. Xiao, et al., Angew. Chem. Int. Ed. 51 (2012) 5714–5717. doi: 10.1002/anie.201201374
37. [37]
  J. Xiang, W.L. Tan, J. Zhang, et al., Macromolecules 55 (2022) 8074–8083. doi: 10.1021/acs.macromol.2c01101
38. [38]
  T. Yao, K. Hirano, T. Satoh, et al., Angew. Chem. Int. Ed. 51 (2012) 775–779. doi: 10.1002/anie.201106825
39. [39]
  J. Radolko, P. Ehlers, P. Langer, Adv. Synth. Catal. 363 (2021) 3616–3654. doi: 10.1002/adsc.202100332
40. [40]
  J. Xiang, W. Tan, J. Zhang, et al., Macromolecules 55 (2022) 8074–8083. doi: 10.1021/acs.macromol.2c01101
41. [41]
  S.N. Steinmann, Y. Mo, C. Corminboeuf, Phys. Chem. Chem. Phys. 13 (2011) 20584–20592. doi: 10.1039/c1cp21055f
42. [42]
  Z. Liu, T. Lu, Q. Chen, Carbon 165 (2020) 468–475. doi: 10.1016/j.carbon.2020.04.099
43. [43]
  D. Geuenich, K. Hess, F. Köhler, et al., Chem. Rev. 105 (2005) 3758–3772. doi: 10.1021/cr0300901
44. [44]
  L. Qin, Y.Y. Huang, B. Wu, et al., Angew. Chem. Int. Ed. 62 (2023) e202304632. doi: 10.1002/anie.202304632
45. [45]
  D.T. Chase, A.G. Fix, S.J. Kang, et al., J. Am. Chem. Soc. 134 (2012) 10349–10352. doi: 10.1021/ja303402p
46. [46]
  A. Maliakal, K. Raghavachari, H. Katz, et al., Chem. Mater. 16 (2004) 4980–4986. doi: 10.1021/cm049060k
47. [47]
  W. Fudickar, T. Linker, J. Am. Chem. Soc. 134 (2012) 15071–15082. doi: 10.1021/ja306056x
48. [48]
  C.J.M. van den Heuvel, J.W. Verhoeven, T.J. de Boer, Recl. des Trav. Chim. des Pays-Bas 99 (1980) 280–284. doi: 10.1002/recl.19800990908
49. [49]
  S. Chien, M. Cheng, K. Lau, et al., J. Phys. Chem. A 109 (2005) 7509. doi: 10.1021/jp0503009
50. [50]
  A.R. Reddy, M. Bendikov, Chem. Commun. 11 (2006) 1179–1181.
1. [1]
  Jianmei Guo , Yupeng Zhao , Lei Ma , Yongtao Wang . Ultra-long room temperature phosphorescence, intrinsic mechanisms and application based on host-guest doping systems. Chinese Journal of Structural Chemistry, 2024, 43(9): 100335-100335. doi: 10.1016/j.cjsc.2024.100335
2. [2]
  Tingting Huang , Zhuanlong Ding , Hao Liu , Ping-An Chen , Longfeng Zhao , Yuanyuan Hu , Yifan Yao , Kun Yang , Zebing Zeng . Electron-transporting boron-doped polycyclic aromatic hydrocarbons: Facile synthesis and heteroatom doping positions-modulated optoelectronic properties. Chinese Chemical Letters, 2024, 35(4): 109117-. doi: 10.1016/j.cclet.2023.109117
3. [3]
  Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
4. [4]
  Jingyuan Yang , Xinyu Tian , Liuzhong Yuan , Yu Liu , Yue Wang , Chuandong Dou . Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching. Chinese Chemical Letters, 2024, 35(8): 109745-. doi: 10.1016/j.cclet.2024.109745
5. [5]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
6. [6]
  Zhefei Hu , Jingwen Liao , Jiawen Zhou , Lulu Zhao , Yanjuan Liu , Yuefei Zhang , Wei Chen , Sheng Tang . A new green approach to synthesizing MIP-202@porous silica microspheres for positional isomer/enantiomer/hydrophilic separation. Chinese Chemical Letters, 2025, 36(1): 109985-. doi: 10.1016/j.cclet.2024.109985
7. [7]
  Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783
8. [8]
  Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe₂O₃/TiO₂ heterojunction for enhanced photo-Fenton activity with low H₂O₂ consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
9. [9]
  Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
10. [10]
  Yunjia Jiang , Lingyao Wang , Yuanbin Zhang . Anion pillared MOFs for challenging hydrocarbon separations. Chinese Journal of Structural Chemistry, 2024, 43(11): 100374-100374. doi: 10.1016/j.cjsc.2024.100374
11. [11]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
12. [12]
  Shunyu Wang , Yanan Zhu , Yang Zhao , Wanli Nie , Hong Meng . Steric effects and electronic manipulation of multiple donors on S₀/S₁ transition of D_n-A emitters. Chinese Chemical Letters, 2025, 36(4): 110555-. doi: 10.1016/j.cclet.2024.110555
13. [13]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
14. [14]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
15. [15]
  Zhengyi Shi , Jie Yin , Yang Xiao , Zhangrong Hou , Fei Song , Jianping Wang , Qingyi Tong , Changxing Qi , Yonghui Zhang . Unprecedented sesquiterpene-polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex Ⅴ. Chinese Chemical Letters, 2024, 35(10): 109458-. doi: 10.1016/j.cclet.2023.109458
16. [16]
  Dongying Fu , Lin Pan , Yanli Ma , Yue Zhang . Bilayered Dion–Jacobson lead-iodine hybrid perovskite with aromatic spacer for broadband photodetection. Chinese Chemical Letters, 2025, 36(2): 109621-. doi: 10.1016/j.cclet.2024.109621
17. [17]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
18. [18]
  Jiayuan Liang , Xin Mi , Songhao Guo , Hui Luo , Kejun Bu , Tonghuan Fu , Menglin Duan , Yang Wang , Qingyang Hu , Rengen Xiong , Peng Qin , Fuqiang Huang , Xujie Lü . Pressure-induced emission in 0D metal halide (EATMP)SbBr5 by regulating exciton-phonon coupling. Chinese Journal of Structural Chemistry, 2024, 43(7): 100333-100333. doi: 10.1016/j.cjsc.2024.100333
19. [19]
  Yu He , Hao Jiang , Shaoxuan Yuan , Jiayi Lu , Qiang Sun . On-surface photo-induced dechlorination. Chinese Chemical Letters, 2024, 35(9): 109807-. doi: 10.1016/j.cclet.2024.109807
20. [20]
  Wu-Yang Liu , Xin-Xiang Lei , Wen-Ji Wang , Jun-Mian Tian , Yu-Qi Gao , Jin-Ming Gao . Hyperforatone A, the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol with a unique bicyclo[5.4.0]undecane core from Hypericum perforatum. Chinese Chemical Letters, 2025, 36(4): 110478-. doi: 10.1016/j.cclet.2024.110478

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(275)
HTML views(3)

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