Citation: Peng-Xia Liang, Dong Wang, Zong-Cheng Miao, Zhao-Kui Jin, Huai Yang, Zhou Yang. Spectral and self-assembly properties of a series of asymmetrical pyrene derivatives[J]. Chinese Chemical Letters, ;2014, 25(2): 237-242. shu

Spectral and self-assembly properties of a series of asymmetrical pyrene derivatives

1.
School of Materials Science and Engineering, University of Science and Technology Beijing, Beijing 100083, China

Corresponding author: Dong Wang, Zhou Yang,
Received Date: 14 August 2013
Available Online: 8 October 2013
Fund Project: This work was partially supported by Beijing Natural Science Foundation (No. 2122042) (No. 2122042)the National Natural Science Fund for Distinguished Young Scholar (No. 51025313). (No. FRF-TP-09-010B)

A series of pyrene derivatives with different asymmetrical substituents were successfully synthesized and characterized. The geometrical electronic structures of the asymmetrical pyrene derivatives were performed by density functional theory (DFT) calculations. The results of photophysical spectra and electrochemical analysis indicated that the optical or electric properties of the pyrene derivatives could be tuned by adjust the π-conjugation lengths of the substituents. Furthermore, through a phase exchange self-assembly method, the highly organized morphologies were observed by SEM.
- Asymmetrical,
- Pyrene,
- Self-assembly
1. [1]
  [1] K.R.J. Thomas, J.T. Lin, Y.T. Tao, et al., Light-emitting carbazole derivatives: potential electroluminescent materials, J. Am. Chem. Soc. 123 (2001) 9404-9411.
2. [2]
  [2] L. Schmidt-Mende, A. Fechtenkätter, K. Müllen, et al., Efficient organic photovoltaics from soluble discotic liquid crystalline materials, Physica E 14 (2002) 263-267.
3. [3]
  [3] C.D. Dimitrakopoulos, P.R.L. Malenfant, Organic thin film transistors for large area electronics, Adv. Mater. 14 (2002) 99-117.
4. [4]
  [4] B. Esembeson, M.L. Scimeca, T. Michinobu, et al., A high-optical quality supramolecular assembly for third-order integrated nonlinear optics, Adv. Mater. 20 (2008) 4584-4587.
5. [5]
  [5] A. Yella, H.W. Lee, H.N. Tsao, et al., Porphyrin-sensitized solar cells with cobalt (II/Ⅲ)-based redox electrolyte exceed 12 percent efficiency, Science 334 (2011) 629-634.
6. [6]
  [6] S. Kawata, Y. Kawata, Three-dimensional optical data storage using photochromic materials, Chem. Rev. 100 (2000) 1777-1788.
7. [7]
  [7] I.D. Tevis, L.C. Palmer, D.J. Herman, Self-assembly and orientation of hydrogenbonded oligothiophene polymorphs at liquid-membrane-liquid interfaces, J. Am. Chem. Soc. 133 (2011) 16486-16494.
8. [8]
  [8] (a) X.J. Zhang, X.H. Zhang, W.S. Shi, et al., Morphology-controllable synthesis of pyrene nanostructures and its morphology dependence of optical properties, J. Phys. Chem. B 109 (2005) 18777-18780; (b) Z.F. Duan, Z.G. Yang, D.J. Liu, et al., Synthesis of two mono-deoxy β-cyclodextrin derivatives as useful tools for confirming DIBAL-H promoted bis-de-O-methylation mechanism, Chin. Chem. Lett. 22 (2011) 819-822; (c) X.M. Wang, H. Yan, X.L. Feng, et al., 1-Pyrenecarboxaldehyde thiosemicarbazone: a novel fluorescent molecular sensor towards mercury (Ⅱ) ion, Chin. Chem. Lett. 21 (2010) 1124-1128.
9. [9]
  [9] Y. Wang, H.M. Wang, Y.Q. Liu, et al., 1-Imino nitroxide pyrene for high performance organic field-effect transistors with low operating voltage, J. Am. Chem. Soc. 128 (2006) 13058-13059.
10. [10]
  [10] W.L. Jia, T.M. Cormick, Q.D. Liu, et al., Diarylamino functionalized pyrene derivatives for use in blue OLEDs and complex formation, J. Mater. Chem. 14 (2004) 3344-3350.
11. [11]
  [11] (a) E.B. Namdas, A. Ruseckas, I.D. Samuel, et al., Photophysics of fac-tris(2- phenylpyridine) iridium(Ⅲ) cored electroluminescent dendrimers in solution and films, J. Phys. Chem. B 108 (2004) 1570-1577; (b) C.C. Kwok, M.S. Wong, Synthesis and light-emitting properties of difunctional dendritic distyrylstilbenes, Macromolecules 34 (2001) 6821-6830.
12. [12]
  [12] (a) J.Y. Hu, M. Era, M.R.J. Elsegood, T. Yamato, Synthesis and photophysical properties of pyrene-based light-emitting monomers: highly pure-blue-fluorescent, cruciform-shaped architectures, Eur. J. Org. Chem. 1 (2010) 72-79; (b) H.J. Zhang, X.J. Xu, W.F. Qiu, et al., Unsymmetrical dendrimers as highly efficient light-emitting materials: synthesis, photophysics, and electroluminescence, J. Phys. Chem. C 112 (2008) 13258-13262.
13. [13]
  [13] S. Bernhardt, M. Kastler, V. Enkelmann, et al., Pyrene as chromophore and electrophore: encapsulation in a rigid polyphenylene shell, Chem. Eur. J. 12 (2006) 6117-6128.
14. [14]
  [14] Z.J. Zhao, S.M. Chen, J.W.Y. Lam, et al., Pyrene-substituted ethenes: aggregationenhanced excimer emission and highly efficient electroluminescence, J. Mater. Chem. 21 (2011) 7210-7216.
15. [15]
  [15] D. Wang, T. Michinobu, One-step synthesis of ladder-type fused poly(benzopentalene) derivatives with tunable energy levels by variable substituents, J. Polym. Sci. Part A: Polym. Chem. 49 (2011) 72-75.
16. [16]
  [16] G. Venkataramana, S. Sankararaman, Synthesis, absorption, and fluorescenceemission properties of 1,3,6,8-tetraethynylpyrene and its derivative, Eur. J. Org. Chem. (2005) 4162-4166.
17. [17]
  [17] S.Y. Chen, X.J. Xu, Y.Q. Liu, et al., New organic light-emitting materials: synthesis, thermal, photophysical, electrochemical, and electroluminescent properties, J. Phys. Chem. C 111 (2007) 1029-1031.
18. [18]
  [18] M. Beinhoff, W. Weigel, M. Jurczok, et al., Synthesis and spectroscopic properties of arene-substituted pyrene derivatives as model compounds for fluorescent polarity probes, Eur. J. Org. Chem. 20 (2001) 3819-3829.
19. [19]
  [19] Y.S. Kim, S.Y. Bae, K.H. Kim, et al., Highly sensitive phototransistor with crystalline microribbons from new p-extended pyrene derivative via solution-phase selfassembly, Chem. Commun. 47 (2011) 8907-8909.
20. [20]
  [20] J.D. Hartgerink, E.R. Zubarev, S.I. Stupp, et al., Supramolecular one-dimensional objects, Curr. Opin. Solid State Mater. Sci. 5 (2001) 355-361.
21. [21]
  [21] M. Supur, Y. Yamada, M.E. El-Khouly, et al., Electron delocalization in onedimensional perylenediimide nanobelts through photoinduced electron transfer, J. Phys. Chem. C 115 (2011) 15040-15047.
1. [1]
  Rongxin Zhu , Shengsheng Yu , Xuanzong Yang , Ruyu Zhu , Hui Liu , Kaikai Niu , Lingbao Xing . Construction of pyrene-based hydrogen-bonded organic frameworks as photocatalysts for photooxidation of styrene in water. Chinese Chemical Letters, 2024, 35(10): 109539-. doi: 10.1016/j.cclet.2024.109539
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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
13. [13]
  Ruoxi Sun , Yiqian Xu , Shaoru Rong , Chunmiao Han , Hui Xu . The Enchanting Collision of Light and Time Magic: Exploring the Footprints of Long Afterglow Lifetime. University Chemistry, 2024, 39(5): 90-97. doi: 10.3866/PKU.DXHX202310001
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
18. [18]
  Xingwen Cheng , Haoran Ren , Jiangshan Luo . Boosting the self-trapped exciton emission in vacancy-ordered double perovskites via supramolecular assembly. Chinese Journal of Structural Chemistry, 2024, 43(6): 100306-100306. doi: 10.1016/j.cjsc.2024.100306
19. [19]
  Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(658)
HTML views(5)

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