Citation: Cao Jie, Liao Chaoqiang, Yang Ling, Zhang Xuejun. Synthesis and Characterization of the Coumarin-Binuclear Zinc Phthalocyanine Formed by Droxynaphthyl Bridge[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 213-217. doi: 10.6023/cjoc201508013 shu

Synthesis and Characterization of the Coumarin-Binuclear Zinc Phthalocyanine Formed by Droxynaphthyl Bridge

1.
College of Science, North University of China, Taiyuan 030051

Corresponding author: Zhang Xuejun, zhangxuejun@nuc.edu.cn
Received Date: 11 August 2015
Revised Date: 2 September 2015

Fund Project: National Natural Science Foundation of China 51272239Shanxi Scholarship Council of China 2015-078National Natural Science Foundation of Shanxi Province 2015011011

Figures(6)

9(10), 16(17), 23(24)-Tris[4-methyl-coumarin-7-yloxy]-2(3)-(1, 5-naphthalene) binuclear zinc phthalocyanine (bi-CPc) based 1, 5-dihydroxynaphthalene, 4-nitro-phthalonitrile, resorcinol, ethyl acetoacetate and zinc acetate on raw material was synthesized. The structures and properties of precursors and bi-CPc were characterized by ¹H NMR, FT-IR, UV-Vis, elemental analysis and thermogravimetric analysis. Results showed that strong π-π^* transition was demonstrated by UV-Vis absorption spectrum of bi-CPc. At the same time, it existed in a form of monomer in solution of N, N-dimethylformamide (DMF) and possessed excellent thermal stability. Redox behavior of bi-CPc was researched by cyclic voltammetry (CV), and energy level of LUMO and HOMO of bi-CPc matched with energy level of nano-TiO₂ after calculating. Through further structural modification, it is expected to use as photosensitive dye with excellent performance for solar cells.
- phthalocyanine,
- binuclear,
- coumarin,
- dye-sensitized solar cells
1. [1]
  O'Regan, B.; Grätzel, M. Nature 1991, 353, 737 doi: 10.1038/353737a0
2. [2]
  Grätzel, M. J. Photochem. Photobiol. A 2004, 164, 34
3. [3]
  He, J.-J.; Chen, Y.-S.; Wang, T.-T.; Zeng, H.-P. Org. Chem. 2012, 32, 472 (in Chinese).
4. [4]
  Hou, Y.-J.; Xie, P.-H.; Zhang, B.-W.; Cao, Y.; Xiao, X.-R.; Wang, W.-B. Inorg. Chem. 1999, 38, 6320. doi: 10.1021/ic990001w
5. [5]
  Horiuchi, T.; Miura, H.; Uchida, S. J. Photochem. Photobiol. A: Chem. 2004, 164, 29. doi: 10.1016/j.jphotochem.2003.12.018
6. [6]
  Hara, K.; Kurashige, M.; Ito, S.; Shinpo, A.; Suga, S.; Sayama, K.; Arakawa, H. Chem. Commun. 2003, 252.
7. [7]
  Karthikeyan, C. S.; Peter, K.; Wietasch, H.; Thelakkat, M.; Energy, M. Sol. Cells 2007, 91, 432.
8. [8]
  Hara, K.; Sayama, K.; Ohga, Y.; Shinpo; Suga, S.; Arakawa, H. Chem. Commun. 2001, 569.
9. [9]
  Kitamura, T.; Ikeda, M.; Shigaki, K.; Inoue, T.; Andenson, N. A.; Ai, X.; Lian, T. Q.; Yanagida, S. Chem. Mater. 2004, 16, 1806. doi: 10.1021/cm0349708
10. [10]
  Hwang, S.; Lee, J. H.; Park, C.; Lee, H.; Kim, C.; Lee, M. H.; Lee, W.; Paka, J.; Kim, K.; Park, N. G.; Kim, C. Chem. Commun. 2007, 4887.
11. [11]
  Hara, K.; Miyamoto, K.; Abe, Y.; Yanagida, M. J. Phys. Chem. B 2005, 109, 23776. doi: 10.1021/jp055572q
12. [12]
  Wang, Y.-Q.; Lu, X.; Wei, X.-D.; Wu, W.-J.; Xie, Y.-S. New J. Chem.2014, 38: 3227. doi: 10.1039/c4nj00651h
13. [13]
  Mathew, S.; Yella, A; Gao, P.; Humphry-Baker, R. Nat. Chem. 2014, 6, 242. doi: 10.1038/nchem.1861
14. [14]
  Takuro, L.; Hirotaka, N.; Naruhiko, M.; Matthew, J. G.; Shogo, M.; Mutsumi, K. Chem. Commun. 2014, 50, 1941. doi: 10.1039/c3cc47714b
15. [15]
  Mao, L.-J.; Tan, Q.-L.; Xing, G.-Q.; Han, M.-L.; Zhang, X.-J. Chin. J. Org. Chem. 2012, 32, 2315 (in Chinese). doi: 10.6023/cjoc201206019
16. [16]
  Kc, C. C.; Stranius, K.; Dsouza, P. J. Chem. Phys. 2013, 117, 763. doi: 10.1021/jp308234j
17. [17]
  Camur, M.; Ahsen, V.; Durmus, M. Photochem. Photobiol. A: Chem. 2011, 219, 217. doi: 10.1016/j.jphotochem.2011.02.014
18. [18]
  Han, L.; Zhou, X.; Ye, Q.; LI, J.-Y.; Gao, J.-R. Chin. J. Org. Chem.2013, 33, 1000 (in Chinese). doi: 10.6023/cjoc201212029
19. [19]
  Peng, Y.-R.; Huang, F.-H. Strait Pharm. J. 2003, 15, 53 (in Chinese).
20. [20]
  Han, M.-L. M.S. Thesis, North University of China, Taiyuan, 2015 (in Chinese).
21. [21]
  Leeuw, D. M.; Simenon, M. M. J.; Brown, A. R. Synth. Met. 1997, 87, 53. doi: 10.1016/S0379-6779(97)80097-5
1. [1]
  Yipeng Zhou , Chenxin Ran , Zhongbin Wu . Metacognitive Enhancement in Diversifying Ideological and Political Education within Graduate Course: A Case Study on “Solar Cell Performance Enhancement Technology”. University Chemistry, 2024, 39(6): 151-159. doi: 10.3866/PKU.DXHX202312096
2. [2]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
3. [3]
  Yixuan Gao , Lingxing Zan , Wenlin Zhang , Qingbo Wei . Comprehensive Innovation Experiment: Preparation and Characterization of Carbon-based Perovskite Solar Cells. University Chemistry, 2024, 39(4): 178-183. doi: 10.3866/PKU.DXHX202311091
4. [4]
  Pengyu Dong , Yue Jiang , Zhengchi Yang , Licheng Liu , Gu Li , Xinyang Wen , Zhen Wang , Xinbo Shi , Guofu Zhou , Jun-Ming Liu , Jinwei Gao . NbSe₂纳米片优化钙钛矿太阳能电池的埋底界面. Acta Physico-Chimica Sinica, 2025, 41(3): 2407025-. doi: 10.3866/PKU.WHXB202407025
5. [5]
  Nengmin ZHU , Wenhao ZHU , Xiaoyao YIN , Songzhi ZHENG , Hao LI , Zeyuan WANG , Wenhao WEI , Xuanheng CHEN , Weihai SUN . Preparation of high-performance CsPbBr₃ perovskite solar cells by the aqueous solution solvent method. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1131-1140. doi: 10.11862/CJIC.20240419
6. [6]
  Zeyuan WANG , Songzhi ZHENG , Hao LI , Jingbo WENG , Wei WANG , Yang WANG , Weihai SUN . Effect of I₂ interface modification engineering on the performance of all-inorganic CsPbBr₃ perovskite solar cells. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1290-1300. doi: 10.11862/CJIC.20240021
7. [7]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
8. [8]
  Xiaoyao YIN , Wenhao ZHU , Puyao SHI , Zongsheng LI , Yichao WANG , Nengmin ZHU , Yang WANG , Weihai SUN . Fabrication of all-inorganic CsPbBr₃ perovskite solar cells with SnCl₂ interface modification. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 469-479. doi: 10.11862/CJIC.20240309
9. [9]
  Mingxuan Qi , Lanyu Jin , Honghe Yao , Zipeng Xu , Teng Cheng , Qi Chen , Cheng Zhu , Yang Bai . 钙钛矿太阳能电池在反向偏压下的电学失效及稳定性研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100088-. doi: 10.1016/j.actphy.2025.100088
10. [10]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
11. [11]
  Chao Liu , Huan Yu , Jiaming Li , Xi Yu , Zhuangzhi Yu , Yuxi Song , Feng Zhang , Qinfang Zhang , Zhigang Zou . Facile synthesis of hierarchical Ti₃C₂/Bi₁₂O₁₇Br₂ Schottky heterojunction with photothermal effect for solar-driven antibiotics photodegradation. Acta Physico-Chimica Sinica, 2025, 41(7): 100075-. doi: 10.1016/j.actphy.2025.100075
12. [12]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
13. [13]
  Fengqiao Bi , Jun Wang , Dongmei Yang . Specialized Experimental Design for Chemistry Majors in the Context of “Dual Carbon”: Taking the Assembly and Performance Evaluation of Zinc-Air Fuel Batteries as an Example. University Chemistry, 2024, 39(4): 198-205. doi: 10.3866/PKU.DXHX202311069
14. [14]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
15. [15]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
16. [16]
  Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
17. [17]
  Xinxin JING , Weiduo WANG , Hesu MO , Peng TAN , Zhigang CHEN , Zhengying WU , Linbing SUN . Research progress on photothermal materials and their application in solar desalination. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1033-1064. doi: 10.11862/CJIC.20230371
18. [18]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
19. [19]
  Jiaxuan Zuo , Kun Zhang , Jing Wang , Xifei Li . 锂离子电池Ni-Co-Mn基正极材料前驱体的形核调控及机制. Acta Physico-Chimica Sinica, 2025, 41(1): 2404042-. doi: 10.3866/PKU.WHXB202404042
20. [20]
  Kun Rong , Cuilian Wen , Jiansen Wen , Xiong Li , Qiugang Liao , Siqing Yan , Chao Xu , Xiaoliang Zhang , Baisheng Sa , Zhimei Sun . Hierarchical MoS₂/Ti₃C₂T_x heterostructure with excellent photothermal conversion performance for solar-driven vapor generation. Acta Physico-Chimica Sinica, 2025, 41(6): 100053-. doi: 10.1016/j.actphy.2025.100053

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1119)
HTML views(138)

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