Effects of Binary Solvent System on Aggregation Behaviors and Photoelectric Properties of Perylene Imide Derivative with Secondary Amine Groups
LONG Tao1,2,YANG Xinguo1,2,LI Siyu1,2,WANG Ying1,2,MAO Fengyu1,2
1 College of Materials Science and Engineering, Hunan University, Changsha 410082, China 2 Key Laboratory for Spray Deposition Technology and Application of Hunan Province, Hunan University, Changsha 410082, China
Abstract: Aperylene imide derivative N,N- 2(2-ethylethylenediamine)-1,6,7,12-4(4-tert-butyl phenylexy)-3,4,9,10-perylene imide (B-PDI-1) containing secondary amine group prepared. The photophysical properties of B-PDI-1 in THF/H2O self-assembly systems with different THF fractions were investigated by UV-vis and fluorescence spectrum.The morphologies and structures of B-PDI-1 in THF/H2O was characterized by SEM and XRD. Cyclic voltammetry (CV) was used to study the influence of binary solvent environment on the electronic structure of aggregates. The electrochemical workstation was used to measure the J-V curve and transient light response of the aggregate, and the photovoltaic perfor-mance was evaluated. The results showed that the absorption of B-PDI-1 in THF/H2O in the UV-vis spectrum showed red-shift phenomenon, and the maximum value reached 35.4 nm when fTHF=10%. With the decrease of fTHF in the THF/H2O binary solvent system, the fluorescence gra-dually decreased, but there was always a trace fluorescence. B-PDI-1 adopted J-type aggregation in THF/H2O.B-PDI-1 form aggregates with distinct morphologies in mixed solutions with different THF/H2O ratios. In solutions with different fTHF, the nanostructures of spiral strip, long oblique quadrilateral, rod shape, spherical shape and long straight nanoribbon are obtained respectively.With the change of fTHF, the mole-cular packing mode is changed, and the perturbation between molecules is mainly manifested in the improvement of HOMO energy level. The difference of energy band of different aggregates causes the color change, and the maximum light wave conversion efficiency is 0.43% at fTHF=10%.
1 Whitesides G M, Mathias J P, Seto C T. Sicence, 1991, 254(5036),1312. 2 Kausik B, Ritaban H, Biman J, et al. Journal of Physical Chemistry C, 2019, 123, 6241. 3 Sahnawaz A, Bapan P, Amba S K N, et al. Scientific Reports, 2017, 7, 9485. 4 Geraldine E, Guy C L, Charl F J F. Chemistry-A European Journal, 2015, 21, 5118. 5 Guo Qiang, Wang Junchao, Zhu Lingyun, et al. Chinese Journal of Chemistry, 2015, 33, 95. 6 Ma Hongchao, Fei Jinbo, Li Qi, et al. Small, 2015, 11,1787. 7 Wang Chao, Chen Qishui, Xu Huaping, et al. Advanced Materials, 2010, 22, 2553. 8 Wang Xin, Zeng Ting, Nourrein Mohamed, et al. RSC Advances, 2017, 7, 26074. 9 Elisa A, Vincenzo G, Rishat D, et al. Physical Chemistry Chemical Phy-sics, 2019, 21, 18300. 10 Seong Hun Yu, Boseok Kang, Gukil An, et al. ACS Applied Materials & Interfaces, 2015, 7,2025. 11 Hu Zhaosheng, Lin Zhenhua, Su Jie, et al. ACS Applied Electronic Materials, 2019, 1, 2030. 12 Zhao Donglin, Wu Qinghe, Cai Zhengxu, et al. Chemistry of Materials, 2016, 28,1139. 13 Eduardo Aluicio-Sarduy, Ranbir Singh, Zhipeng Kan, et al.ACS Applied Materials & Interfaces, 2015, 7,8687. 14 Ranbir S, Ester G, Marta M M, et al. Organic Electronics, 2014, 15,1347. 15 Chiu Tienlung, Chuang Kaihsiang, Lin Chifeng, et al. Thin Solid Films, 2009, 517,3712. 16 Bapan Pramanik, Julfikar Hassan Mondal, Nilotpal Singha, et al. ChemPhysChem, 2017, 18,245. 17 Manuel G R, Marta M V, Víctor N F, et al. Journal of Materials Chemistry C, 2013, 1,1182. 18 Shao Yu, Yin Guangzhong, Ren Xiangkui, et al. RSC Advances, 2017, 7, 6530. 19 Mohammed J F, Mark A P, Jessica B, et al. Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy, 2016, 153, 124. 20 Li Mei, Xu Jiaru, Zeng Yang, et al. Dyes and Pigments, 2017, 139,79. 21 Qu Jianfei, Mu Zhao, Lai Hanjian,et al. ACS Applied Energy Materials. 2018, 1, 833. 22 Chen Shuai, Slattum Paul, Wang Chuanyi, and et al. Chemical Reviews, 2015, 115, 11967. 23 Kausik Bag, Pradip Kumar Sukul, Dines Chandra Santra, et al. RSC Advances, 2016, 6, 34027. 24 Li Siyu, Long Tao, Wang Ying, et al. Dyes and Pigments, 2020, 173, 107896. 25 Lv Baozhong, You Shusen, Li Pengyu, et al. Chemistry-A European Journal, 2017, 23, 397. 26 Peter Spenst, Frank Wîrthner. Angewandte Chemie International Edition, 2015, 54,10165. 27 Li N, Athanassios Z P, et al. Langmuir, 2017, 33, 6021. 28 Joseph K G, Emma J A, Robert A. Chemical Communications, 2012, 48,7961. 29 Shang Xiaobo, Song Inho, Ohtsu Hiroyoshi, et al. Scientific Reports, 2017, 7,5508. 30 Erin R J, Shahar K, Paula M S,et al. Journal of the American Chemical Society, 2010, 132,6498. 31 Dai Yulan, Guo Meiyuan, Peng Jingdong, et al. Chemical Physics Letters, 2013, 556,230. 32 Peter W M, Christoph S, Konstantin D, et al. Journal of the American Chemical Society, 2018, 140,5427. 33 Juliusz S. Synthetic Metals, 2018, 235,125. 34 Pradhan S, Redwine J, Mcleskey J J T, et al, Thin Solid Films, 2014, 562, 423.