Synthesis of the First Generation π-Conjugate Unsymmetrical Dendrimers with Different Cores

doi:10.3724/SP.J.1095.2013.20466

Chinese Journal of Applied Chemistry

• Full Papers • Previous Articles Next Articles

Synthesis of the First Generation π-Conjugate Unsymmetrical Dendrimers with Different Cores

PENG Xiaochun^*, WU Jianhua, XIAO Zhuping, XIE Bitao, WU Fang, ZHAO Hanshuang

(College of Chemistry and Chemical Engineering,Jishou University,Jishou 416000,China)

Received:2012-10-18 Revised:2013-02-01 Published:2013-08-10 Online:2013-08-10
Contact: Peng xiaochun
Supported by:
湖南省自然科学基金（13JJ2030）、林产化工工程湖南省重点实验室开放基金（JDZ201104）资助项目

Abstract

Abstract: 4,5-Bis(3′,5′-di-tert-butylphenylethynyl)-2-methoxyphenol(dendron) was synthesized from 3,5-di-tertbutyl phenol, trifluoromethanesulfonic anhydride and 4,5-diethynyl-2-methoxyphenol. The phenolic hydroxyl group was subsequently esterified by trifluoromethanesulfonic anhydride. By coupling different chromophores(biphenyl, azobenzene, anthracene, pyrene) on the as-obtained sulfonic esters, π-conjugate unsymmetrical dendrimers with different cores were obtained. 1H NMR, 13C NMR spectroscopy, FT-IR spectroscopy and element analysis were deployed to characterize the resultant products. The solubility of the dendrimers reveals that, compared to the cores(varieties of chromophores), all dendrimers are soluble in most common organic solvents. Meanwhile, the dendrimers show improved thermostability. These two characters make the dendrimers to be easily blended with other materials or added into equipments.

Key words: unsymmetrical conjugate dendrimers, chromophores coupling, synthesis, characterization

CLC Number:

O625.1

PENG Xiaochun*, WU Jianhua, XIAO Zhuping, XIE Bitao, WU Fang, ZHAO Hanshuang. Synthesis of the First Generation π-Conjugate Unsymmetrical Dendrimers with Different Cores[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20466.

References

[1] Tomalia D A. Birth of a New Macromolecular Architecture:Dendrimer as Quantized Building Blocks for Nanoscale Synthetic Polymer Chemistry[J]. Prog Polym Sci,2005,30:294-324.

[2] WU Anqi,WANG Song,HUANG Haiqin. Research Development of Dendritic-linear Hybrid Copolymers at Home and Abroad[J]. Mater Rev,2008,22(6):54-57,60(in Chinese).

吴安琪,王嵩,黄海琴. 树枝状线性杂化共聚物国内外研究进展[J]. [HTK]材料导报[HTSS],2008,22(6):54-57,60.

[3] ZHAO Liwen,FAN Qinghua,ZHOU Haifeng. Study of Dendrimers as Supports for Organic Synthesis Progress in Chemistry[J]. Prog Chem,2006,18(1):317-320(in Chinese).

赵立文,范青华,周海峰. 树状大分子在有机合成中的应用[J]. [HTK]化学进展[HTSS],2006,18(1):317-320.

[4] LIU Haifeng,WANG Yurong,REN Yan. Development of Dendrimers′ Practical Using Research[J]. Polym Bull,2005,6(3):116-118(in Chinese).

刘海峰,王玉荣,任艳. 树枝状聚合物的应用研究进展[J]. [HTK]高分子通报[HTSS],2005,6(3):116-118.

[5] Vgtle F,Gestermann R,Hesse H,et al. Functional Dendrimers[J]. Prog Polym Sci,2000,25:987-1041.

[6] Hecht S. Functionalizing the Interior of Dendrimers:Synthetic Challenges and Applications[J]. J Polym Sci Part A:Polym Chem,2003,41(8):1047-1058.

[7] Akai I,Miyanari K,Shimamotol T,et al. Rapid Energy Transfer in a Dendrimer Having π-Conjugated Light-harvesting Antennas[J]. New J Phys,2008,10:125024.

[8] Wang J L,Zhou Y,Li Y F,et al. Solution-Processable Gradient Red-Emitting π-Conjugated Dendrimers Based on Benzothiadiazole as Core:Synthesis, Characterization, and Device Performances[J]. J Org Chem,2009,74:7449-7456.

[9] Liu R,Xiao Q,Li Y H,et al. Phenylene Ethynylene Azobenzenes with Symmetrical Peripheral Chromophores:Synthesis, Optical Properties and Photoisomerization Behaviors Study[J]. Dyes Pigm,2011,92:626-632.

[10] Raquel Gimenez,Milagros Pinol,Jose Luis Serrano. Luminescent Liquid Crystals Derived from 9,10-Bis(Phenylethynyl)-anthracene[J]. Chem Mater,2004,16:1377-1383.

[11] Oh J W,Lee Y O,Kim T H. Enhancement of Electrogenerated Chemiluminescence and Radical Stability by Peripheral Multidonors on Alkynylpyrene Derivatives[J]. Angew Chem,Int Ed,2009,48(14):2522-2524.

[12] Wu K C,Ku P J,Lin C S. The Photophysical Properties of Dipyrenylbenzenes and Their Application as Exceedingly Efficient Blue Emitters for Electroluminescent Devices[J]. Adv Funct Mater,2008,18(1):67-75.

[13] Stéphanie Leroy-Lhez,Frédéric Fages. Synthesis and Photophysical Properties of a Highly Fluorescent Ditopic Ligand Based on 1,6-Bis(ethynyl)pyrene as Central Aromatic Core[J]. Eur J Org Chem,2005,13:2684-2688.

[1]	Jia-Zheng LI, Shu-Zhong HE. Research Progress of Total Synthesis of Polygalolides [J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 615-624.
[2]	Zhen-Bang LIU, Shuo ZHANG, Yu BAO, Ying-Ming MA, Wei-Qi LIANG, Wei WANG, Ying HE, Li NIU. Progress of Application Research on Cheminformatics in Deep Learning [J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 360-373.
[3]	Yang LIU, Hai-Bao ZHANG, Qiang CHEN. Optimization of Process Parameters for Ammonia Synthesis by Nanosecond Pulsed Dielectric Barrier Discharge Plasma [J]. Chinese Journal of Applied Chemistry, 2023, 40(2): 268-276.
[4]	Rong CAO, Jie-Zhen XIA, Man-Hua LIAO, Lu-Chao ZHAO, Chen ZHAO, Qi WU. Theoretical Research Progress of Single Atom Catalysts in Electrochemical Synthesis of Ammonia [J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 9-23.
[5]	Dan MENG, Kai-Yuan ZHENG, Shan-Shan CHEN, Zhao-Long ZHUO, Li-Li WANG. Preparation and Luminescence Properties of Silicon and Nitrogen Co⁃doped Carbon Dots Phosphors [J]. Chinese Journal of Applied Chemistry, 2022, 39(11): 1766-1773.
[6]	WU Zhi-Qiang, HAN Xin-Ning, LIU Yang, WANG Gang, ZHAN Hai-Juan, LIU Wan-Yi. Research Progress on Synthesis of Bis(indolyl)methanes under Aqueous or Solvent-free Catalysis [J]. Chinese Journal of Applied Chemistry, 2021, 38(8): 881-896.
[7]	BO Chun-Hui, JIANG Wei-Jia, WANG Yu-Gao, SHI Li-Hong, DONG Chuan. Research Progress on Synthesis of Coal-based Carbon Quantum Dots [J]. Chinese Journal of Applied Chemistry, 2021, 38(7): 767-788.
[8]	LIU Yang, ZHANG Hai-Bao, CHEN Qiang. Research Progress on Ammonia Synthesis Using Low Temperature Plasma [J]. Chinese Journal of Applied Chemistry, 2021, 38(6): 622-636.
[9]	LIU Yu-Ting, SUN Jia-Xi, YIN Da-Wei. Research Progress on the Synthesis and Application of Ferroncene-based Polymers [J]. Chinese Journal of Applied Chemistry, 2021, 38(4): 343-366.
[10]	XIE Zhi-Qi, ZHANG Ting, LI Ying-Wei, WANG Zhou-Jun, DAI Fei, ZHANG Rui-Rui, LIU Rui-Xia. Effect of Synthesis Conditions of Vanadium Phosphorus Oxygen (VPO) Catalyst on Catalytic Performance for Selective Oxidation of Butane [J]. Chinese Journal of Applied Chemistry, 2021, 38(4): 414-421.
[11]	GAO Feng, XU Zi-Di, GUAN Chun-Qian, WANG Yan, ZANG Yun-Hao, QU Jiang-Ying. Green Controllable Synthesis of Sulfur/Graphene Aerogel and Performance of Lithium Sulfur Battery [J]. Chinese Journal of Applied Chemistry, 2021, 38(4): 439-446.
[12]	BI Yipiao, GONG Xue, YANG Fa, RUAN Mingbo, SONG Ping, XU Weilin. Polyvalent MnO_x/C Electrocatalyst for Highly Efficient Nitrogen Reduction Reaction [J]. Chinese Journal of Applied Chemistry, 2020, 37(9): 1048-1055.
[13]	ZHANG Baohua, SHI Lanxiang. One-Pot Synthesis of Aryl/Heteroaryl Aminomethylene Bisphosphonates [J]. Chinese Journal of Applied Chemistry, 2020, 37(8): 877-882.
[14]	MENG Yating, JIAO Yuan, ZHANG Yuan, GAO Yifang, LU Wenjing, LIU Yang, DONG Chuan. Synthesis of Red Emission Fluorescent Carbon Dots and Its Application for Detection of Persulfate [J]. Chinese Journal of Applied Chemistry, 2020, 37(6): 719-725.
[15]	JIANG Xiaoxiao, ZHU Jinwen, LIAO Xiaofeng, YIN Weiwei, GAO Peng, YANG Changlin, WANG Feng. Synthesis of Oligo-L-Tyrosine via Bromelain [J]. Chinese Journal of Applied Chemistry, 2020, 37(2): 175-181.

Synthesis of the First Generation π-Conjugate Unsymmetrical Dendrimers with Different Cores

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments