Synthesis, Self-Assembly and Spectroscopic Analysis of 9,10-Bis((4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)ethynyl)anthracene

doi:10.11944/j.issn.1000-0518.2015.02.140164

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (2): 177-182.DOI: 10.11944/j.issn.1000-0518.2015.02.140164

• Full Papers • Previous Articles Next Articles

Synthesis, Self-Assembly and Spectroscopic Analysis of 9,10-Bis((4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)ethynyl)anthracene

JIN Guangri^a, ZHU Jikai^a, ZHONG Keli^b, CHEN Tie^a, JIN Longyi^{a, *}

aDepartment of Chemistry,College of Science,Yanbian University,and Key Laboratory for Organism Resources of the Changbai Mountain and Functional Molecules,Ministry of Education,Yanbian University,Yanji,Jilin 133002,China
bFood Safety Key Lab of Liaoning Province,Engineering and Technology Research Center of Food Preservation,Processing and Safety Control of Liaoning Province,College of Chemistry,Chemical Engineering and Food Safety,Bohai University,Jinzhou,Liaoning 121013,China

Received:2014-05-06 Revised:2014-07-09 Published:2015-02-10 Online:2015-02-10
Contact: Corresponding author:JIN Longyi, professor; Tel/Fax:0433-2732316; E-mail:lyjin@ybu.edu.cn; Research interests:self-assembly of supramolecule
Supported by:
; Supported by the National Natural Science Foundation of China(No.21164013, No.21304009), Open Project of State Key Laboratory for Supramolecular Structure and Materials(No.sklssm201430)

Abstract

Abstract:

9,10-Bis((4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)ethynyl)anthracene(1) was synthesized by Sonogashira coupling. Its structure was characterized by ¹H NMR and MALDI-TOF mass spectroscopy. The self-assembling behavior of compound 1 was investigated by means of differential scanning calorimetry(DSC), thermal polarized optical microscopy(POM), and small-angle X-ray scattering(SAXS) at the bulk state. Compound 1 self-assembled into smectic A phase(SmA) in the solid state. Spectroscopic analysis suggested that compound 1 inherited the characteristic of high fluorescence quantum yield(Φ_f) of disubstituted anthracenes. The title compound 1 is a kind of photoluminescence materials with good performance.

Key words: self-assembly, anthracene, fluorescence quantum yield, smectic A phase, Sonogashira coupling reaction

CLC Number:

O625.1

JIN Guangri, ZHU Jikai, ZHONG Keli, CHEN Tie, JIN Longyi. Synthesis, Self-Assembly and Spectroscopic Analysis of 9,10-Bis((4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)ethynyl)anthracene[J]. Chinese Journal of Applied Chemistry, 2015, 32(2): 177-182.

References

[1] HU Rui,GUO Xudong,YANG Guoqiang, et al . Investigation on the Property of the Excited State Intramolecular Proton Transfer Compounds and its Application as Fluorescence Chemical Sensor[J]. Imag Sci Photochem ,2013,31(5):335-348(in Chinese). 胡睿,郭旭东,杨国强,等. 激发态分子内质子转移化合物的性能及作为荧光化学传感器的应用研究[J]. 影像科学与光化学,2013,31(5):335-348.
[2] HUANG Yanqin,REN Houji,CAO Guoyi, et al . Supramolecular Self-assembly of π-Conjugated Systems[J]. Sci China Chem ,2013,43(2):125-141(in Chinese). 黄艳琴,任厚基,曹国益,等. π-共轭体系超分子自组装[J]. 中国科学:化学,2013,43(2):125-141.
[3] Rajamalli P,Prasad E. Low Molecular Weight Fluorescent Organogel for Fluoride Ion Detection[J]. Org Lett ,2011,13(14):3714-3717.
[4] SUN Mei,DING Dayong,HU Hanmei, et al . Synthesis of an Blue Fluorescence Compound with Two-photon Property[J]. Chinese J Appl Chem ,2006,23(8):933-935(in Chinese). 孙梅,丁大勇,胡寒梅,等. 具有双光子活性的蓝色发光材料的合成[J]. 应用化学,2006,23(8):933-935.
[5] Tanabe K,Suzui Y,Hasegawa M, et al . Full-Color Tunable Photoluminescent Ionic Liquid Crystals Based on Tripodal Pyridinium, Pyrimidinium, and Quinolinium Salts[J]. J Am Chem Soc ,2012,134(12):5652-5661.
[6] Yazaki S,Funahashi M,Kato T. An Electrochromic Nanostructured Liquid Crystal Consisting of π-Conjugated and Ionic Moieties[J]. J Am Chem Soc ,2008,130(40):13206-13207.
[7] Zhang H C,Guo E Q,Zhang Y L, et al . Donor-Acceptor-Substituted Anthracene-Centered Cruciforms:Synthesis, Enhanced Two-Photon Absorptions, and Spatially Separated Frontier Molecular Orbitals[J]. Chem Mater ,2009,21(21):5125-5135.
[8] Yang W J,Seo M S,Wang X Q, et al . Two-Photon Absorption Properties of 9,10-Disubstituted 2,6-Bis( p -dihexylaminostyryl)anthracene Derivatives. Effect of 9,10-Substituents[J]. J Fluoresc ,2008,18(2):403-411.
[9] Yang W J,Kim D Y,Jeong M Y, et al . Two-Photon Absorption Properties of 2,6-Bis(styryl) anthracene Derivatives:Effects of Donor-Acceptor Substituents and the π Center[J]. Chem- Eur J ,2005,11(14):4191-4198.
[10] WU Bianpeng,XU Jianhua,YANG Shuying, et al . Synthesis and Quantitative Analysis of Compound of 9,10-Bis(6- t -butyl-2-naphthyl)anthenace by Grinard Reaction[J]. J Tianjin Inst Urban Const ,2005,11(4):291-297(in Chinese). 吴边鹏,许建华,杨淑英,等. 电致发光材9,10-二(6-叔丁基-2-萘基)蒽的合成和纯度分析[J]. 天津城市建设学院学报,2005,11(4):291-297.
[11] DING Bangdong,ZHU Wenqing,JIANG Xueyin, et al . Synthesis and Electroluminescence Characteristics of Anthracene Derivatives[J]. Semicond Optoelectron ,2008,29(5):680-683(in Chinese). 丁邦东,朱文清,蒋雪茵,等. 蒽衍生物的合成及其电致发光特性[J]. 半导体光电,2008,29(5):680-683.
[12] Willinger K,Fischer K,Kisselev R, et al . Synthesis, Spectral, Electrochemical and Photovoltaic properties of Novel Heteroleptic Polypyridyl Ruthenium(Ⅱ) Donor-antenna Dyes[J]. J Mater Chem ,2009,19(30):5364-5376.
[13] Zhu J K,Zhong K L,Jin L Y, et al . Synthesis and Self-assembly of Oligomers Containing Cruciform 9,10-Bis(arylethynyl)anthracene Unit:Formation of Supramolecular Nanostructures Based on Rod-Length-Dependent Organization[J]. Tetrahedron ,2014,70(6):1230-1235.
[14] Hirose T,Matsuda K. Self-assembly of Amphiphilic Fluorescent Dyes Showing Aggregate-induced Enhanced Emission:Temperature Dependence of Molecular Alignment and Intermolecular Interaction in Aqueous Environment[J]. Chem Commun ,2009,45(39):5832-5834.

[1]	Yu-Zhu CHEN, Si-Si LIU, Meng-Meng ZHANG, Xiang-De LIN, Dong-Dong ZENG. Polyurethane Dressing Based on Antibacterial Chitosan/Carboxymethyl Cellulose Composite Drug Coating [J]. Chinese Journal of Applied Chemistry, 2023, 40(2): 252-260.
[2]	Kai WANG, Hai-Kuan YANG, Hui-Lan LIU, Jia-Min LU, Chen ZHANG. Synthesis and Gelation Properties of Stigmasterol‑Based Supramolecular Gelators [J]. Chinese Journal of Applied Chemistry, 2022, 39(9): 1453-1463.
[3]	Xin HE, Cai-Yun JIANG, Tao DING, Yu-Ping WANG. Reserch Progress of Preparation of Ordered Surface Enhanced Raman Scattering Substrate [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1167-1176.
[4]	Wei-Qiang ZHANG, Chen WANG, Yu-Rong ZHAO, Dong WANG, Ji-Qian WANG, Hai XU. Research Progress of Regulation of Driving Forces in Short Peptide Supramolecular Self‑Assembly [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1190-1201.
[5]	Zi-Li LI, Xing-Ran XU, Jiang-Hao ZHAN, Xiao-Hua HU, Zi-Ying ZHANG, Shi-Sheng XIONG. Advanced Materials for Lithography [J]. Chinese Journal of Applied Chemistry, 2022, 39(6): 859-870.
[6]	HU Xiao-Hua, XIONG Shi-Sheng. Advanced Lithography: Directed Self-Assembly [J]. Chinese Journal of Applied Chemistry, 2021, 38(9): 1029-1078.
[7]	TIAN Xin, LAI Han-Wen, LIU Ya-Dong, JI Sheng-Xiang. Analysis of Defects in Block Copolymer Films by a Convolution Algorithm [J]. Chinese Journal of Applied Chemistry, 2021, 38(9): 1199-1208.
[8]	WANG Hou-Chen, ZHOU Li, LIU Yang, CHEN Ming-Yue, SHI Tie-Sheng. Research Progress on the Molecular Designs of Building Blocks for Supramolecular Aggregates and Self-Assemblies [J]. Chinese Journal of Applied Chemistry, 2021, 38(6): 615-621.
[9]	LIU Jiao, ZOU Peng-Fei, LI Ping, ZHANG Xiao, WANG Xin-Xin, GAO Yuan-Yuan, LI Li-Li. Research Progress of the Peptide-Based Self-assembled Nanomaterials Against Microbial Resistance [J]. Chinese Journal of Applied Chemistry, 2021, 38(5): 546-558.
[10]	CHEN Song-Hua, CHEN Xin, LIU Yong-Qi, HE Mei-Yun, FU Shan-Shan, PENG Li, YANG Ji-En. Preparation and Optical Waveguide Property of Benzothiadiazole-Containing One Dimensional Micro-nanowires [J]. Chinese Journal of Applied Chemistry, 2021, 38(11): 1479-1485.
[11]	WU Yu, LIU Jia-Cheng. Preparation and Characterization of Dye-sensitized Solar Cells by Inverted Coordination Self-assembly [J]. Chinese Journal of Applied Chemistry, 2021, 38(11): 1494-1502.
[12]	Long-Fei LUO, Yu-Jie LI, Zhi-Hao SHEN, Shi-Jun ZHENG, Xing-He FAN. Progress in Self⁃assembly and Photo⁃responsiveness of Thin Films of Azobenzene⁃Based Liquid Crystalline Block Copolymers [J]. Chinese Journal of Applied Chemistry, 2021, 38(10): 1238-1254.
[13]	Ai-Hua CHEN, Cheng-Yun ZHANG, Zi-Chao DENG, Ya-Lan SUN. Structure Control of Liquid Crystalline Block Copolymers in Liquid⁃Phase Self⁃assembly [J]. Chinese Journal of Applied Chemistry, 2021, 38(10): 1255-1267.
[14]	Meng-Wei LI, Hong-Yan WANG, Ying-Ying WANG, Xiao-Ying KANG, Mei-Fang LIU, Yu-Lan CHEN. Supramolecular Self⁃Assembly of Azobenzene⁃4，4'⁃dicarboxylic Acid Derivatives in Water [J]. Chinese Journal of Applied Chemistry, 2021, 38(10): 1362-1370.
[15]	GONG Hui, KANG Yu, ZHANG Rong, REN Guodong, HOU Xiaoyu, ZHANG Min, LI Lihong, LIU Wen, WANG Haojiang, DIAO Haipeng. Preparation of Nitrogen-Doped Carbon Dots for Highly Sensitive Detection of Amoxicillin [J]. Chinese Journal of Applied Chemistry, 2020, 37(2): 227-234.

Synthesis, Self-Assembly and Spectroscopic Analysis of 9,10-Bis((4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)ethynyl)anthracene

RichHTML

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments