Citation: Zhichao Wang, Qianli Ma, Xuan Huang, Tian Zhang, Jiawei Shao, Xinglin Zhang, Qian Shen, Xiaochen Wang, Jinjun Shao. S/Se-embedded acenaphthylene-imide-containing polycyclic heteroaromatic hydrocarbon[J]. Chinese Chemical Letters, ;2022, 33(1): 271-275. doi: 10.1016/j.cclet.2021.06.072 shu

S/Se-embedded acenaphthylene-imide-containing polycyclic heteroaromatic hydrocarbon

Zhichao Wang ^a ,
Qianli Ma ^a ,
Xuan Huang ^a ,
Tian Zhang ^a ,
Jiawei Shao ^b ,
Xinglin Zhang ^a ,
Qian Shen ^{a, *} ,
Xiaochen Wang ^{c, *} ,
Jinjun Shao ^{a, *}

a.
Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Nanjing Tech University (NanjingTech), Nanjing 211800, China
b.
Department of Chemistry, National University of Singapore, Singapore 117543, Singapore
c.
School of Materials Science & Engineering, Shaanxi Normal University, Xi'an 710119, China

iamqshen@njtech.edu.cn

wangxc@snnu.edu.cn

iamjjshao@njtech.edu.cn

Received Date: 28 April 2021
Revised Date: 23 June 2021
Accepted Date: 25 June 2021
Available Online: 2 July 2021

Figures(5)

Acenapththylene-imide (AnI), similar to naphthalene diimide (NDI), is an outstanding building block for organic functional materials and has gained a lot of research attention. Herein, Sulphur and Selenium-embedded AnI-containing polycyclic aromatic hydrocarbon molecules, AnI-SQ and AnI-SeQ, with [1, 2, 5]thiadiazolo [3, 4-g]quinoxaline (SQ) and [1, 2, 5]selenadiazolo [3, 4-g]quinoxaline (SeQ) are designed and synthesized with low-lying LUMO energy levels. The absorption and emission of AnI-SQ and AnI-SeQ displayed a bathochromic shift upon protonation of the C = N bond. Besides, theoretical calculation indicates remarkable rigid planar backbones for both AnI-SQ and AnI-SeQ. Through self-assembly with polymeric Pluronic® F-127, corresponding hydrophilic nanoparticles (NPs) were prepared with low cytotoxicity. And AnI-SQ NPs could be applied for in vitro two-photon fluorescence imaging.
- Acenaphthylene-imide,
- Polycyclic aromatic hydrocarbons,
- Protonation,
- Selenium,
- Condensation
1. [1]
  X. Cui, C. Xiao, T. Winands, et al., J. Am. Chem. Soc. 140(2018) 12175-12180. doi: 10.1021/jacs.8b07305
2. [2]
  C. Liu, Y. Ni, X. Lu, G. Li, J. Wu, Acc. Chem. Res. 52(2019) 2309-2321. doi: 10.1021/acs.accounts.9b00257
3. [3]
  J. Yang, Y. Jiang, Z. Tu, et al., Adv. Funct. Mater. 29(2019) 1804839. doi: 10.1002/adfm.201804839
4. [4]
  D. Ji, T. Li, W. Hu, H. Fuchs, Adv. Mater. 31(2019) 1806070. doi: 10.1002/adma.201806070
5. [5]
  Q. Yue, W. Liu, X. Zhu, J. Am. Chem. Soc. 142(2020) 11613-11628. doi: 10.1021/jacs.0c04084
6. [6]
  M. Stepien, E. Gonka, M. Zyla, N. Sprutta, Chem. Rev. 117(2017) 3479-3716. doi: 10.1021/acs.chemrev.6b00076
7. [7]
  H. Zhang, K. Li, L. Li, Chin. Chem. Lett. 30(2019) 1063-1066. doi: 10.1016/j.cclet.2019.03.017
8. [8]
  B. Zhao, H. Wang, C. Han, et al., Angew. Chem. Int. Ed. 59(2020) 19042-19047. doi: 10.1002/anie.202008885
9. [9]
  J. Yuan, Y. Zhang, L. Zhou, et al., Joule 3(2019) 1140-1151. doi: 10.1016/j.joule.2019.01.004
10. [10]
  Z. Zhao, C. Chen, W. Wu, et al., Nat. Commun. 10(2019) 768. doi: 10.1038/s41467-019-08722-z
11. [11]
  D. Chen, Q. Yu, X. Huang, H. Dai, et al., Small 16(2020) 2001059. doi: 10.1002/smll.202001059
12. [12]
  D. Chen, Z. Wang, H. Dai, et al., Small Methods 4(2020) 2000013.
13. [13]
  F. Xiao, B. Cao, L. Wen, et al., Chin. Chem. Lett. 31(2020) 2516-2519. doi: 10.1016/j.cclet.2020.06.038
14. [14]
  C. Liu, S. Zhang, J. Li, et al., Angew. Chem. Int. Ed. 58(2019) 1638-1642. doi: 10.1002/anie.201810541
15. [15]
  C. Ji, W. Cheng, Q. Yuan, et al., Acc. Chem. Res. 52(2019) 2266-2277. doi: 10.1021/acs.accounts.9b00221
16. [16]
  H. Dai, Q. Shen, J. Shao, et al., The Innovation 2(2021) 100082.
17. [17]
  B. Joseph, V.K. Sagarika, C. Sabu, et al., J. Bioresour. Bioprod. 5(2020) 231-247. doi: 10.1016/j.jobab.2020.10.001
18. [18]
  H. Xu, D. Zhang, J. Li, J. Bioresour. Bioprod. 4(2019) 177-182. doi: 10.12162/jbb.v4i3.006
19. [19]
  Z. Wang, Q. Peng, X. Huang, et al., Dyes Pigm. 185(2021) 108877. doi: 10.1016/j.dyepig.2020.108877
20. [20]
  S. Seifert, D. Schmidt, K. Shoyama, F. Wurthner, Angew. Chem. Int. Ed. 56(2017) 7595-7600. doi: 10.1002/anie.201702889
21. [21]
  Y.J. Hwang, H. Li, B. Courtright, S. Subramaniyan, S.A. Jenekhe, Adv. Mater. 28(2016) 124-131. doi: 10.1002/adma.201503801
22. [22]
  K. Zhou, X. Qiu, L. Xu, et al., ACS Appl. Mater. Interfaces 12(2020) 14905-14913. doi: 10.1021/acsami.0c01069
23. [23]
  K. Shoyama, M. Mahl, M.A. Niyas, et al., J. Org. Chem. 84(2019) 142-149.
24. [24]
  H. Li, T. Earmme, S. Subramaniyan, S.A. Jenekhe, Adv. Energy Mater. 5(2015) 1402041. doi: 10.1002/aenm.201402041
25. [25]
  H. Li, Y.J. Hwang, T. Earmme, et al., Macromolecules 48(2015) 1759-1766. doi: 10.1021/ma502042k
26. [26]
  H. Li, Y.J. Hwang, B. Courtright, et al., Adv. Mater. 27(2015) 3266-3272. doi: 10.1002/adma.201500577
27. [27]
  J. Shao, X. Guo, N. Shi, et al., Sci. China Mater. 61(2018) 497-507. doi: 10.1007/s40843-019-9452-1
28. [28]
  F. Verstraeten, S. Gielen, P. Verstappen, et al., J. Mater. Chem. C 8(2020) 10098-10103. doi: 10.1039/D0TC01435D
29. [29]
  C. Costa, J. Farinhas, J. Avó, et al., New J. Chem. 13(2019) 5202-5213. doi: 10.1039/C8NJ06012F
30. [30]
  S. Li, C. Yin, R. Wang, et al., ACS Appl. Mater. Interfaces 12(2020) 20281-20286. doi: 10.1021/acsami.0c03769
31. [31]
  X. Du, J. Qi, Z. Zhang, et al., Chem. Mater. 24(2012) 2178-2185. doi: 10.1021/cm3008733
32. [32]
  F. Liu, S. Wu, Y. Zhang, X. Hao, L. Ding, Sci. Bull. 65(2020) 698-701. doi: 10.1016/j.scib.2020.02.014
33. [33]
  H. Sun, Y. Tang, C.W. Koh, et al., Adv. Mater. 31(2019) 1807220. doi: 10.1002/adma.201807220
34. [34]
  K. Kise, A. Osuka, Chem. Eur. J. 25(2019) 15493-15497. doi: 10.1002/chem.201904151
35. [35]
  D. Tian, Y. Zhou, Z. Li, et al., ChemistrySelect 2(2017) 8137-8145. doi: 10.1002/slct.201701051
36. [36]
  Z. Cheng, T. Zhang, W. Wang, et al., Chin. Chem. Lett. 32(2021) 1580-1585. doi: 10.1016/j.cclet.2021.02.017
37. [37]
  A.L. Antaris, H. Chen, K. Cheng, et al., Nat. Mater. 14(2015) 235-242. doi: 10.1038/nmat4476
38. [38]
  L. Xu, H. Zhu, G. Long, et al., J. Mater. Chem. C 3(2015) 9191-9196. doi: 10.1039/C5TC01657F
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沈阳化工大学材料科学与工程学院沈阳 110142