Synthesis and Properties of Chiral Conjugated Polymer Incorporating (R)- and (S)-1,1'-Binaphthyl and Oxadiazole Units

Abstract

Abstract: Chiral conjugated polymers P-1 and P-2 were obtained by the polymerization of (S)-6,6'-dibromo-2,2'-bisbutoxy-1,1'-binaphthyl and (R)-6,6'-dibromo-2,2'-bisbutoxy-1,1'-binaphthyl with 2,5-bis(tri-n-butyltinphenyl)-1,3,4-oxadiazole(M-2) respectively via Stille coupling reaction catalyzed by Pd(PPh₃)₄. Both monomers and polymers were characterized by NMR, MS, FTIR, UV, DSC-TG, fluorescent spectroscopy, GPC and CD spectra. The butoxy substitutents on binaphthyl rings as a side chain of the polymers can improve the solubility in organic solvents and facile electro-optical sensors. 1,3,4-Oxadiazole unit is a better chromophore, and has good hole-transporting and stability for oxygen and heat. The polymers can emit very strong blue fluorescence. They are expected to have the potential application in the materials of interesting electro-optical molecular sensors.

Key words: (R)/(S)-BINOL, Chiral polymer, Fluorescence spectrum, CD spectrum, Stille reaction

CLC Number:

O631.1

TrendMD:

CHEN Ling-Wu, CHENG Yi-Xiang, SONG Jin-Feng, ZOU Xiao-Wei. Synthesis and Properties of Chiral Conjugated Polymer Incorporating (R)- and (S)-1,1'-Binaphthyl and Oxadiazole Units[J]. Chem. J. Chinese Universities, 2005, 26(9): 1743.

[1]	MA Xiangying, LIAO Yanjun, QIN Fanghong, YIN Yuanhao, HUANG Zaiyin, CHEN Qifeng. Study on the Photocatalytic Performance of Carbon Doped g-C₃N₄ Based on in situ Photomicrocalorimeter-fluorescence Spectrometry [J]. Chem. J. Chinese Universities, 2020, 41(11): 2526.
[2]	LIU Feng, LI Qinfang, OUYANG Kunbing, YANG Nianfa. Application of Two Chiral BINOL Polymers in Asymmetric Epoxidation Reaction ^† [J]. Chem. J. Chinese Universities, 2019, 40(8): 1628.
[3]	BAI Lei,HUO Shuhui,CHEN Jing,LU Xiaoquan. Squaramide Fluorescence Probe for Chiral Recognition of α-Amino Acids^† [J]. Chem. J. Chinese Universities, 2019, 40(1): 41.
[4]	LI Yang, LI Zhiwen, ZHU Junfei, LIU Shihui, HE Junlin. Construction of Pyrenyl Pairs in dsDNA: Fluorescent Properties of Multiple Pyrenyl-attached dsDNAs Through 7-Substituted 8-Aza-7-deaza-2'-deoxyadenosine Analogues^† [J]. Chem. J. Chinese Universities, 2018, 39(10): 2206.
[5]	WAN Ting, LI Xingxing, HUANG Zaiyin, QIU Jiangyuan, ZUO Chen, TAN Xuecai. In-situ Photocatalytic Process of Rhodamine B over g-C₃N₄@Ag₃PO₄ Nanocomposites Based on Photomicrocalorimeter-fluorescence Spectrometry^† [J]. Chem. J. Chinese Universities, 2017, 38(12): 2226.
[6]	QIAN Liwei, LI Ji, SONG Wenqi, HU Xiaoling, GUAN Ping. Utilizing Macromolecular Chain as Functional Monomer and Crosslinker to Imprint BSA with Preserving the Structural Integrity of Template^† [J]. Chem. J. Chinese Universities, 2016, 37(11): 2092.
[7]	ZHANG Jing, JIANG Yuliang, CHENG Yu, GU Weijin, WANG Bingxiang. Microwave Synthesis of Glycerol Carbon Quantum Dots and Its Application in Fe³⁺ Probe^† [J]. Chem. J. Chinese Universities, 2016, 37(1): 54.
[8]	XIANG Junfeng, YI Pinggui, YU Xianyong, CHEN Jian, HAO Yanlei, REN Zhiyong. Excited-state Proton Transfer of 2-(2-Hydroxyphenyl)benzothiazole in the Confined Nanocavity^† [J]. Chem. J. Chinese Universities, 2015, 36(4): 654.
[9]	DONG Lu, YI Zhongsheng, WU Zhiwei, WANG Haiyang, ZHANG Aiqian. Mechanism Study on the Interaction Between 2'-Hydroxy-2,4-dibromo Diphenyl Ethers and Human Serum Albumin Based on Spectroscopic Methods and Computional Simulations^† [J]. Chem. J. Chinese Universities, 2015, 36(3): 516.
[10]	WANG Zhiming, FENG Ying, LI Hui, SONG Xiaohui, LU Ping. Preparation and Characterization of Phenanthroimidazole-based Derivatives with Ether Linkage at N1-Phenyl^† [J]. Chem. J. Chinese Universities, 2014, 35(8): 1691.
[11]	WANG Manyuan, ZHANG Chao, LI Jing, LI Zhaoxia, GONG Muxin. Interaction of Antimalarial Components Combination from Artemisia annua L. with Bovine Serum Albumin^† [J]. Chem. J. Chinese Universities, 2014, 35(2): 309.
[12]	LIN Hai-Bin, ZHENG Lin, LIN Yu-Qin, ZHOU Zhao-Hui. Study of Interaction Between Bovine Serum Albumin and Cobalt Complexes of Phenanthroline and Nitrilotriacetate by Fluorescence Spectrometry [J]. Chem. J. Chinese Universities, 2013, 34(8): 1818.
[13]	FENG Xuan, ZHANG Tan, BIAN Liu-Jiao. Distribution and Transition of Stable Conformations of Denatured Hen Egg White Lysozymes During Their Refolding in Guanidine Hydrochloride Solutions [J]. Chem. J. Chinese Universities, 2013, 34(2): 336.
[14]	LIU Chun-Yu, WANG Shao-Yan, XU Shu-Ping, XU Wei-Qing. SERS and EEM Fluorescence Spectral Distinction of Sudan Ⅰ and Paprika Red in Food [J]. Chem. J. Chinese Universities, 2013, 34(11): 2505.
[15]	TANG Yu-Lin, GAO Zhan, XU Hong, HE Jian-Zhi, DONG Yi-Han, ZHENG Yi-Zhi. Interaction of Copper(II) Ion with SALI3-2 [J]. Chem. J. Chinese Universities, 2013, 34(1): 128.

Synthesis and Properties of Chiral Conjugated Polymer Incorporating (R)- and (S)-1,1'-Binaphthyl and Oxadiazole Units

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments