Citation: Yuchuan Xiao, Fangjian Cai, Xuan Peng, Xiyuan Kang, Peng Lei, Xin Li, Haijun Xu, Xunwen Xiao, Bin Tu, Qingdao Zeng. Aza-BODIPY molecular assembly at the liquid-solid interface driven by Br…F—BF interactions[J]. Chinese Chemical Letters, ;2021, 32(11): 3566-3569. doi: 10.1016/j.cclet.2021.02.066 shu

Aza-BODIPY molecular assembly at the liquid-solid interface driven by Br…F—BF interactions

Yuchuan Xiao ^{a, c, d, 1} ,
Fangjian Cai ^{b, 1} ,
Xuan Peng ^{a, d, 1} ,
Xiyuan Kang ^b ,
Peng Lei ^{a, d} ,
Xin Li ^e ,
Haijun Xu ^{b, f, **,} ,
Xunwen Xiao ^{c, ***,} ,
Bin Tu ^{a, *,} ,
Qingdao Zeng ^{a, d, *,}

a.
CAS Key Laboratory of Standardization and Measurement for Nanotechnology, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology (NCNST), Beijing 100190, China
b.
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
c.
School of Materials and Chemical Engineering, Ningbo University of Technology, Ningbo 315211, China
d.
Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, China
e.
CAS Center for Excellence in Nanoscience, Beijing Key Laboratory of Micro-Nano Energy and Sensor, Beijing Institute of Nanoenergy and Nanosystems, Chinese Academy of Sciences, Beijing 100083, China
f.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453002, China

^**

^***

xuhaijun@njfu.edu.cn

xunwenxiao@nbut.edu.cn

tub@nanoctr.cn

zengqd@nanoctr.cn

Received Date: 11 January 2021
Revised Date: 19 February 2021
Accepted Date: 26 February 2021
Available Online: 1 March 2021

Figures(3)

In this work, two aza-BODIPY derivatives, 3,5-diphenyl-1,7-di(p-dodecyloxyphenyl)-aza-BODIPY (CJF) and 3,5-di(p-bromophenyl-1,7-di(p-dodecyloxyphenyl)-aza-BODIPY (2Br-CJF) acted as model molecules to form the self-assembly monolayers on the solid-liquid interface. With the utilizing of scanning tunnelling microscope (STM), we demonstrated that intermolecular Br…F—BF interactions existed in 2Br-CJF self-assembly structure and played an important role in strengthening the stability of 2Br-CJF self-assembly structure. This result is supported by density functional theory (DFT) calculation.
- Aza-BODIPY,
- STM,
- Br…F interaction,
- Self-assembly,
- Surface assembly
1. [1]
  K. Reichenbacher, H.I. Suss, J. Hulliger, Chem. Soc. Rev. 34 (2005) 22-30. doi: 10.1039/B406892K
2. [2]
  T.T. Bui, S. Dahaoui, C. Lecomte, G.R. Desiraju, E. Espinosa, Angew. Chem. Int. Ed. 48 (2009) 3838-3841. doi: 10.1002/anie.200805739
3. [3]
  S.K. Nayak, M.K. Reddy, T.N.G. Row, D. Chopra, Cryst. Growth Des. 11 (2011) 1578-1596. doi: 10.1021/cg101544z
4. [4]
  G.R. Desiraju, R. Parthasarathy, J. Am. Chem. Soc. 111 (1989) 8725-8726. doi: 10.1021/ja00205a027
5. [5]
  V.R. Pedireddi, D.S. Reddy, B.S. Goud, et al., J. Chem. Soc. Perkin Trans. 2 (1994) 2353-2360. doi: 10.1039/P29940002353
6. [6]
  E. Albright, J. Cann, A. Decken, S. Eisler, CrystEngComm 19 (2017) 1024-1027. doi: 10.1039/C6CE02339H
7. [7]
  J.S. Ovens, D.B. Leznoff, CrystEngComm 20 (2018) 1769-1773. doi: 10.1039/C7CE02167D
8. [8]
  S.A. Adonin, M.A. Bondarenko, A.S. Novikov, et al., CrystEngComm 21 (2019) 6666-6670. doi: 10.1039/C9CE01106D
9. [9]
  F. Silly, J. Phys. Chem. C 117 (2013) 20244-20249. doi: 10.1021/jp4057626
10. [10]
  Z. Guo, P. Yu, K. Sun, et al., Phys. Chem. Chem. Phys. 19 (2017) 31540-31544. doi: 10.1039/C7CP06027K
11. [11]
  B. Zha, J. Li, J. Wu, X. Miao, M. Zhang, New J. Chem. 43 (2019) 17182-17187. doi: 10.1039/C9NJ04726C
12. [12]
  J. Hou, B. Tu, Q. Zeng, C. Zhan, J. Yao, Chin. Chem. Lett. 31 (2020) 353-356. doi: 10.1016/j.cclet.2019.07.029
13. [13]
  X. Gong, J. Zhang, S. Jiang, Chem. Comm. 56 (2020) 3054-3057. doi: 10.1039/C9CC08768K
14. [14]
  F. Guan, Z. Song, F. Xin, et al., J. Bioresour. Bioprod. 5 (2020) 37-43. doi: 10.1016/j.jobab.2020.03.004
15. [15]
  D.W. Wei, H. Wei, A.C. Gauthier, et al., J. Bioresour. Bioprod. 5 (2020) 1-15. doi: 10.1016/j.jobab.2020.03.001
16. [16]
  A. Mukherjee, A. Sanz-Matias, G. Velpula, et al., Chem. Sci. 10 (2019) 3881-3891. doi: 10.1039/C8SC04499F
17. [17]
  B. Zha, M. Dong, X. Miao, et al., Nanoscale 9 (2017) 237-250. doi: 10.1039/C6NR07693A
18. [18]
  B. Zha, X. Miao, P. Liu, Y. Wu, W. Deng, Chem. Commun. 50 (2014) 9003-9006. doi: 10.1039/C4CC03687E
19. [19]
  Q.N. Zheng, X.H. Liu, T. Chen, et al., J. Am. Chem. Soc. 137 (2015) 6128-6131. doi: 10.1021/jacs.5b02206
20. [20]
  R. Gutzler, O. Ivasenko, C. Fu, et al., Chem. Commun. 47 (2011) 9453-9455. doi: 10.1039/c1cc13114a
21. [21]
  M. Dong, K. Miao, J. Wu, et al., J. Phys. Chem. C 123 (2019) 4349-4359. doi: 10.1021/acs.jpcc.8b12176
22. [22]
  A. Loudet, K. Burgess, Chem. Rev. 107 (2007) 4891-4932. doi: 10.1021/cr078381n
23. [23]
  N. Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 41 (2012) 1130-1172. doi: 10.1039/C1CS15132K
24. [24]
  T. Bura, N. Leclerc, S. Fall, et al., J. Am. Chem. Soc. 134 (2012) 17404-17407. doi: 10.1021/ja3072513
25. [25]
  W. Liu, A. Tang, J. Chen, et al., ACS Appl. Mater. Interfaces 6 (2014) 22496-22505. doi: 10.1021/am506585u
26. [26]
  J. Xu, W. Liu, Y. Geng, et al., Nanoscale 9 (2017) 2579-2584. doi: 10.1039/C6NR08234C
27. [27]
  J. Xu, Y. Li, L. Wang, et al., Chin. Chem. Lett. 30 (2019) 767-770. doi: 10.1016/j.cclet.2018.09.019
28. [28]
  J. Li, X. Zu, Y. Qian, et al., Chin. Chem. Lett. 31 (2020) 10-18. doi: 10.1016/j.cclet.2019.04.032
29. [29]
  J. Li, Y. Qian, W. Duan, Q. Zeng, Chin. Chem. Lett. 30 (2019) 292-298. doi: 10.1016/j.cclet.2018.05.037
30. [30]
  Q. Xue, Y. Zhang, R. Li, et al., Chin. Chem. Lett. 30 (2019) 2355-2358. doi: 10.1016/j.cclet.2019.09.027
31. [31]
  J. Hou, H. Dai, Z. Zhang, et al., Langmuir 33 (2017) 400-406. doi: 10.1021/acs.langmuir.6b03567
32. [32]
  X. Zhu, Y. Geng, H. Xiao, et al., Langmuir 34 (2018) 5169-5173. doi: 10.1021/acs.langmuir.7b04293
33. [33]
  J.P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 77 (1996) 3865-3868. doi: 10.1103/PhysRevLett.77.3865
34. [34]
  J.M. MacLeod, J.A. Lipton-Duffin, D. Cui, S. De Feyter, F. Rosei, Langmuir 31 (2015) 7016-7024. doi: 10.1021/la5048886
35. [35]
  H. Sun, A. Horatscheck, V. Martos, et al., Angew. Chem. Int. Ed. 56 (2017) 6454-6458. doi: 10.1002/anie.201700520
36. [36]
  H.G. Wallnoefer, T. Fox, K.R. Liedl, C.S. Tautermann, Phys. Chem. Chem. Phys. 12 (2010) 14941-14949. doi: 10.1039/c0cp00607f
37. [37]
  I.S. Youn, D.Y. Kim, J.W. Cho, et al., J. Phys. Chem. A 120 (2016) 9305-9314. doi: 10.1021/acs.jpca.6b09395
38. [38]
  L.N. Anderson, F.W. Aquino, A.E. Raeber, X. Chen, B.M. Wong, J. Chem. Theory Comput. 14 (2018) 180-190. doi: 10.1021/acs.jctc.7b01078
1. [1]
  Hongwei Ma , Fang Zhang , Hui Ai , Niu Zhang , Shaochun Peng , Hui Li . Integrated Crystallographic Teaching with X-ray,TEM and STM. University Chemistry, 2024, 39(3): 5-17. doi: 10.3866/PKU.DXHX202308107
2. [2]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
3. [3]
  Lulu Cao , Yikun Li , Dongxiang Zhang , Shuai Yue , Rong Shang , Xin-Dong Jiang , Jianjun Du . Engineering aggregates of julolidine-substituted aza-BODIPY nanoparticles for NIR-II photothermal therapy. Chinese Chemical Letters, 2024, 35(12): 109735-. doi: 10.1016/j.cclet.2024.109735
4. [4]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974
5. [5]
  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. Chinese Chemical Letters, 2024, 35(10): 109446-. doi: 10.1016/j.cclet.2023.109446
6. [6]
  Yuwen Zhu , Xiang Deng , Yan Wu , Baode Shen , Lingyu Hang , Yuye Xue , Hailong Yuan . Formation mechanism of herpetrione self-assembled nanoparticles based on pH-driven method. Chinese Chemical Letters, 2025, 36(1): 109733-. doi: 10.1016/j.cclet.2024.109733
7. [7]
  Jingqi Xin , Shupeng Han , Meichen Zheng , Chenfeng Xu , Zhongxi Huang , Bin Wang , Changmin Yu , Feifei An , Yu Ren . A nitroreductase-responsive nanoprobe with homogeneous composition and high loading for preoperative non-invasive tumor imaging and intraoperative guidance. Chinese Chemical Letters, 2024, 35(7): 109165-. doi: 10.1016/j.cclet.2023.109165
8. [8]
  Keyang Li , Yanan Wang , Yatao Xu , Guohua Shi , Sixian Wei , Xue Zhang , Baomei Zhang , Qiang Jia , Huanhua Xu , Liangmin Yu , Jun Wu , Zhiyu He . Flash nanocomplexation (FNC): A new microvolume mixing method for nanomedicine formulation. Chinese Chemical Letters, 2024, 35(10): 109511-. doi: 10.1016/j.cclet.2024.109511
9. [9]
  Xuanyu Wang , Zhao Gao , Wei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757
10. [10]
  Xian Yan , Huawei Xie , Gao Wu , Fang-Xing Xiao . Boosted solar water oxidation steered by atomically precise alloy nanocluster. Chinese Chemical Letters, 2025, 36(1): 110279-. doi: 10.1016/j.cclet.2024.110279
11. [11]
  Bing Niu , Honggao Huang , Liwei Luo , Li Zhang , Jianbo Tan . Coating colloidal particles with a well-defined polymer layer by surface-initiated photoinduced polymerization-induced self-assembly and the subsequent seeded polymerization. Chinese Chemical Letters, 2025, 36(2): 110431-. doi: 10.1016/j.cclet.2024.110431
12. [12]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
13. [13]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
14. [14]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
15. [15]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
16. [16]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
17. [17]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
18. [18]
  Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
19. [19]
  Yujuan Zhao , Zaiwang Zhao . Monolayer mesoporous nanosheets with surface asymmetry via a dual-emulsion-directed monomicelle assembly. Chinese Journal of Structural Chemistry, 2024, 43(2): 100238-100238. doi: 10.1016/j.cjsc.2024.100238
20. [20]
  Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO₂F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(497)
HTML views(54)

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