Citation: Yan Zhu, Jia Liu, Meiheng Lv, Tingting Wang, Dongxiang Zhang, Rong Shang, Xin-Dong Jiang, Jianjun Du, Guiling Wang. Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation[J]. Chinese Chemical Letters, ;2024, 35(10): 109446. doi: 10.1016/j.cclet.2023.109446 shu

Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation

Yan Zhu ^{a, 1} ,
Jia Liu ^{b, 1} ,
Meiheng Lv ^a ,
Tingting Wang ^a ,
Dongxiang Zhang ^a ,
Rong Shang ^d ,
Xin-Dong Jiang ^{a, *,} ,
Jianjun Du ^{c, *,} ,
Guiling Wang ^{b, *,}

a.
Liaoning & Shenyang Key Laboratory of Functional Dye and Pigment, Shenyang University of Chemical Technology, Shenyang 110142, China
b.
Department of Cell Biology, China Medical University, Shenyang 110122, China
c.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
d.
Department of Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 7398526, Japan

xdjiang@syuct.edu.cn

dujj@dlut.edu.cn

glingwang@cmu.edu.cn

Received Date: 7 October 2023
Revised Date: 19 December 2023
Accepted Date: 21 December 2023
Available Online: 22 December 2023

Figures(6)

Spin-orbit, charge-transfer intersystem crossing (SOCT-ISC) can directly overcome the disadvantages of the traditional heavy-atom effect and improve the generation efficiency of reactive oxygen species (ROS). Since orthogonal molecular orbitals of donor-acceptor (D-A) pairs favor the SOCT-ISC transition, herein aza-borondipyrromethenes (aza-BODIPYs) with 1,7-di-anthracyl groups (An-azaBDP) was successfully prepared, owing to steric hindrance to produce a big dihedral angle between the two molecular orbital (MO) planes. Moreover, according to density functional theory (DFT) and time-dependent density functional theory (TDDFT), the energy difference between the S₁-T₁ orbitals of An-azaBDP is small and more inclined towards ISC. An-azaBDP can effectively generate singlet oxygen under light irradiation. An-azaBDP with light irradiation can induce apoptosis in SW620 cells, and can serve as a potential candidate for the treatment of cancer cells and tumors.
- Orthogonal configuration,
- Anthracene,
- Heavy-atom-free,
- Aza-BODIPY,
- Singlet oxygen
1. [1]
  M.A.T. Rogers, J. Chem. Soc. (1943) 590–596.
2. [2]
  S. Li, M. Lv, J. Wang, et al., Mater. Adv. 3 (2022) 1254–1262. doi: 10.1039/D1MA01052B
3. [3]
  R. Li, J. Ren, D. Zhang, et al., Mater. Today Bio 16 (2022) 100446. doi: 10.1016/j.mtbio.2022.100446
4. [4]
  X. Jiang, S. Yue, K. Chen, et al., Chin. Chem. Lett. 30 (2019) 2271–2273. doi: 10.1016/j.cclet.2019.07.027
5. [5]
  M. Liu, S. Ma, M. She, et al., Chin. Chem. Lett. 30 (2019) 1815–1824. doi: 10.1016/j.cclet.2019.08.028
6. [6]
  R. Li, Y. Du, W. Guo, et al., Dyes Pigm. 179 (2020) 108351. doi: 10.1016/j.dyepig.2020.108351
7. [7]
  V. -N. Nguyen, Z. Zheng, J. Yoon, et al., Chem. Soc. Rev. 51 (2022) 3324–3340. doi: 10.1039/D1CS00647A
8. [8]
  J. Yin, X. Jiang, G. Sui, et al., J. Mater. Chem. B 9 (2021) 7461–7471. doi: 10.1039/D1TB01155C
9. [9]
  F.Z. Li, J.F. Yin, G.C. Kuang, Coord. Chem. Rev. 448 (2021) 214157. doi: 10.1016/j.ccr.2021.214157
10. [10]
  C. Li, Y. Xu, L. Tu, et al., Chem. Sci. 13 (2022) 6541–6549. doi: 10.1039/D2SC01518H
11. [11]
  Outersterp R E van, J. Oosterhout, C.R. Gebhardt, et al., ACS Appl. Bio Mater. 95 (2023) 3406–3413.
12. [12]
  D. Chen, Z. Zhong, Q. Ma, et al., ACS Appl. Mater. Interfaces 12 (2020) 26914–26925. doi: 10.1021/acsami.0c05021
13. [13]
  H. Luo, S. Zhao, J. Transp. Geogr. 90 (2021) 102920. doi: 10.1016/j.jtrangeo.2020.102920
14. [14]
  L.J. Schipper, L.J. Zeverijn, M.J. Garnett, et al., Cancer Discov. 12 (2022) 1634–1641. doi: 10.1158/2159-8290.CD-21-0612
15. [15]
  C. Ma, T. Zhang, Z. Xie, J. Mater. Chem. B 9 (2021) 7318–7327. doi: 10.1039/D1TB00855B
16. [16]
  B.C. Wilson, R.A. Weersink, Photochem. Photobio. 96 (2020) 219–231. doi: 10.1111/php.13184
17. [17]
  R. Zheng, S. Zhang, H. Zeng, et al., J. Natl. Cancer Inst. 2 (2022) 1–9.
18. [18]
  D. Ma, S. Hou, C. Bae, et al., Chin. Chem. Lett. 32 (2021) 3886–3889. doi: 10.1016/j.cclet.2021.05.048
19. [19]
  C. Liu, X. Ji, Z. Yu, et al., J. Med. Chem. 66 (2023) 7205–7220. doi: 10.1021/acs.jmedchem.2c01653
20. [20]
  C. Li, H. Tan, R. Lu, et al., Nanophotonics 11 (2022) 5077–5088. doi: 10.1515/nanoph-2022-0417
21. [21]
  J. Yan, T. Gao, Z. Lu, et al., ACS Appl. Mater. Interfaces 13 (2021) 27749–27773. doi: 10.1021/acsami.1c06818
22. [22]
  J. Treekoon, T. Pewklang, K. Chansaenpak, et al., Org. Biomol. Chem. 19 (2021) 5867–5875. doi: 10.1039/D1OB00400J
23. [23]
  E. Caruso, M.C. Malacarne, E. Marras, et al., Bioorg. Med. Chem. 28 (2020) 115737. doi: 10.1016/j.bmc.2020.115737
24. [24]
  Y. Liu, G. Liu, W. Zhou, et al., Angew. Chem. Int. Ed. 135 (2023) e202309786. doi: 10.1002/ange.202309786
25. [25]
  Z. Ji, J. Zheng, Y. Ma, et al., Small 19 (2023) 2207888. doi: 10.1002/smll.202207888
26. [26]
  L. Wang, A. Mei, N. Li, et al., Chin. Chem. Lett. 35 (2024) 108974. doi: 10.1016/j.cclet.2023.108974
27. [27]
  C. Ye, S. Zhang, D. Zhang, et al., Chin. Chem. Lett. 34 (2023) 108223. doi: 10.1016/j.cclet.2023.108223
28. [28]
  H. Liang, M. Lu, Z. Mahmood, et al., Angew. Chem. Int. Ed. 62 (2023) e202312600. doi: 10.1002/anie.202312600
29. [29]
  C. Li, T. Sun, X. Li, et al., ACS Appl. Nano Mater. 5 (2022) 18691–18696. doi: 10.1021/acsanm.2c04459
30. [30]
  J. Piskorz, W. Porolnik, M. Kucinska, et al., Chem. Med. Chem. 16 (2021) 399–411. doi: 10.1002/cmdc.202000529
31. [31]
  Z. Shi, X. Han, W. Hu, et al., Chem. Soc. Rev. 49 (2020) 7533–7567. doi: 10.1039/D0CS00234H
32. [32]
  W. Hu, Y. Lin, X.F. Zhang, et al., Dyes Pigm. 164 (2019) 139–147. doi: 10.1016/j.dyepig.2019.01.019
33. [33]
  Y. Zhang, Z. Yang, X. Zheng, et al., Dyes Pigm. 178 (2020) 108348. doi: 10.1016/j.dyepig.2020.108348
34. [34]
  W. Sun, X. Wang, Z. Cheng, et al., Biomed. Pharmacother. 158 (2023) 114071. doi: 10.1016/j.biopha.2022.114071
35. [35]
  Y. Yan, A.A. Sukhanov, M.H. Bousquet, et al., J. Phys. Chem. B 125 (2021) 6280–6295. doi: 10.1021/acs.jpcb.1c03189
36. [36]
  V.N. Nguyen, J. Ha, C.W. Koh, et al., Chem. Mater. 33 (2021) 7889–7896. doi: 10.1021/acs.chemmater.1c02776
37. [37]
  Y. Dong, B. Dick, J. Zhao, Org. Lett. 22 (2020) 5535–5539. doi: 10.1021/acs.orglett.0c01903
38. [38]
  J. Li, X. Du, X. Zhou, et al., Adv. Healthc. Mater. 12 (2023) 2301022. doi: 10.1002/adhm.202301022
39. [39]
  M.A. Filatov, S. Karuthedath, P.M. Polestshuk, et al., ChemPhotoChem 2 (2018) 606–615. doi: 10.1002/cptc.201800020
40. [40]
  S.R. Zarcone, H.J. Yarbrough, M.J. Neal, et al., New J. Chem. 46 (2022) 4483–4496. doi: 10.1039/D1NJ05976A
41. [41]
  K. Chen, Y. Dong, X. Zhao, et al., Front. Chem. 7 (2019) 821. doi: 10.3389/fchem.2019.00821
42. [42]
  D. Yang, L. Sun, L. Xue, et al., J. Innov. Opt. Health Sci. 15 (2022) 2250004. doi: 10.1142/S1793545822500043
43. [43]
  A. Olesund, V. Gray, J. Martensson, et al., J. Am. Chem. Soc. 143 (2021) 5745–5754. doi: 10.1021/jacs.1c00331
44. [44]
  Z. Wang, L. Huang, Y. Yan, et al., Angew. Chem. Int. Ed. 132 (2020) 16248–16255. doi: 10.1002/ange.202005269
45. [45]
  J.T. Buck, A.M. Boudreau, A. DeCarmine, et al., Chem 5 (2019) 138–155. doi: 10.1016/j.chempr.2018.10.001
46. [46]
  J.T. Ly, K.F. Presley, T.M. Cooper, et al., Phys. Chem. Chem. Phys. 23 (2021) 12033–12044. doi: 10.1039/D0CP05904H
47. [47]
  M.A. Filatov, S. Karuthedath, P.M. Polestshuk, et al., J. Am. Chem. Soc. 139 (2017) 6282–6285. doi: 10.1021/jacs.7b00551
48. [48]
  Y. Luo, K. Zhang, Z. Ding, et al., Nat. Commun. 13 (2022) 6892. doi: 10.1038/s41467-022-34573-2
49. [49]
  H. Willigen, J. Phys. Chem. 100 (1996) 3312–3316. doi: 10.1021/jp953176+
50. [50]
  L. Yang, Y. Liu, W. Liu, et al., Bio. Med. Chem. Lett. 25 (2015) 5716–5719. doi: 10.1016/j.bmcl.2015.10.091
51. [51]
  J. Zou, L. Li, J. Zhu, et al., Adv. Mater. 33 (2021) 2103627. doi: 10.1002/adma.202103627
52. [52]
  H. Lu, J. Mack, T. Nyokong, et al., Coord. Chem. Rev. 318 (2016) 1–15. doi: 10.1016/j.ccr.2016.03.015
53. [53]
  M. Poddar, P. Gautam, Y. Rout, et al., Dyes Pigm. 146 (2017) 368–373. doi: 10.1016/j.dyepig.2017.07.017
54. [54]
  J. Tao, D. Sun, L. Sun, et al., Dyes Pigm. 168 (2019) 166–174. doi: 10.1016/j.dyepig.2019.04.054
55. [55]
  G. Tarafdar, U.K. Pandey, S. Sengupta, et al., Sol. Energy 186 (2019) 215–224. doi: 10.1016/j.solener.2019.04.093
56. [56]
  P.E. Kesavan, R.N. Behera, S. Mori, et al., J Fluoresc. 27 (2017) 2131–2144. doi: 10.1007/s10895-017-2152-9
57. [57]
  A. Kokalj, Corros. Sci. 180 (2021) 109016. doi: 10.1016/j.corsci.2020.109016
58. [58]
  J. Killoran, L. Allen, D.F. O'Shea, et al., Chem. Commun. (2002) 1862–1863.
59. [59]
  A. Gorman, J. Killoran, D.F. O'Shea, et al., J. Am. Chem. Soc. 126 (2004) 10619–10631. doi: 10.1021/ja047649e
60. [60]
  S. Ahmed, D.J. Kalita, J. Mol. Graph. Model. 100 (2020) 107631. doi: 10.1016/j.jmgm.2020.107631
61. [61]
  T. Bai, T. Chu, J. Mol. Liq. 309 (2020) 113145. doi: 10.1016/j.molliq.2020.113145
62. [62]
  Y. Liu, P. Bhattarai, X. Chen, et al., Chem. Soc. Rev. 48 (2019) 2053–2108. doi: 10.1039/C8CS00618K
63. [63]
  Y. Xiao, F. Cai, X. Peng, et al., Chin. Chem. Lett. 32 (2021) 3566–3569. doi: 10.1016/j.cclet.2021.02.066
64. [64]
  X. Zhang, A.A. Sukhanov, J. Zhao, et al., Chem. Sci. 14 (2023) 5014–5027. doi: 10.1039/D3SC00854A
65. [65]
  L. Huang, X. Cui, J. Zhao, et al., Chem. Eur. J. 19 (2013) 17472–17482. doi: 10.1002/chem.201302492
66. [66]
  K. Zamojc, M. Zdrowowicz, P. Niedzialkowski, et al., Free Radic. Res. 51 (2017)38–46. doi: 10.1080/10715762.2016.1262541
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