Synthesis and photophysical properties of benzo[c]thiophene, p-phenylene-, triphenylamine-, and pyrene-based vinylenes

被引:6
|
作者
Nandakumar, Meganathan [1 ]
Sankar, Elumalai [1 ]
Mohanakrishnan, Arasambattu K. [1 ]
机构
[1] Univ Madras, Sch Chem, Dept Organ Chem, Guindy Campus, Chennai 600025, Tamil Nadu, India
关键词
Benzo[c]thiophene; Horner-Wadsworth-Emmons reaction; Michaelis-Arbuzov reaction; phosphonate ester; pyrene; triphenylamine; vinylene; ORGANIC SEMICONDUCTORS; CONJUGATED POLYMERS; ENERGY-LEVEL; DERIVATIVES; PERFORMANCE; DONOR; TRANSISTORS; COPOLYMERS;
D O I
10.1080/00397911.2016.1228111
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of benzo[c]thiophenyl/p-phenylenyl/pyrenyl phosphonate esters has been achieved using ZnBr2-catalyzed Michaelis-Arbuzov reaction of corresponding benzyl alcohol/bromides at room temperature. Horner-Wadsworth-Emmons reaction of the phosphonate esters with aryl/heteroaryl aldehydes in the presence of t-BuOK furnished the vinylenes in good yields. The absorption and emission characteristics of the synthesized vinylenes were also reported. [GRAPHICS]
引用
收藏
页码:1810 / 1819
页数:10
相关论文
共 14 条
  • [1] Pyrene-based asymmetric hexaarylbenzene derivatives: Synthesis, crystal structures, and photophysical properties
    Liu, Yiwei
    Mao, Xiaoyu
    Wang, Xiaohui
    Bai, Jie
    Zhang, Jun
    Feng, Xing
    Islam, Md. Monarul
    Elsegood, Mark R. J.
    Wang, Chuan-Zeng
    Yamato, Takehiko
    JOURNAL OF LUMINESCENCE, 2022, 243
  • [2] Photophysical properties of new p-phenylene- and benzodithiophene-based fluorophores for luminescent solar concentrators (LSCs)
    Albano, Gianluigi
    Colli, Tony
    Biver, Tarita
    Aronica, Laura Antonella
    Pucci, Andrea
    DYES AND PIGMENTS, 2020, 178
  • [3] Synthesis, Structure and Photophysical Properties of Pyrene-based [5] Helicenes: an Experimental and Theoretical Study
    Wang, Chuan-Zeng
    Kihara, Rie
    Feng, Xing
    Thuery, Pierre
    Redshaw, Carl
    Yamato, Takehiko
    CHEMISTRYSELECT, 2017, 2 (04): : 1436 - 1441
  • [4] Synthesis, Structural, and Photophysical Properties of the First Member of the Class of Pyrene-Based [4]Helicenes
    Hu, Jian-Yong
    Feng, Xing
    Paudel, Arjun
    Tomiyasu, Hirotsugu
    Rayhan, Ummey
    Thuery, Pierre
    Elsegood, Mark R. J.
    Redshaw, Carl
    Yamato, Takehiko
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (26) : 5829 - 5837
  • [5] Pyrene functionalized triphenylamine-based dyes: synthesis, photophysical properties and applications in OLEDs
    Zhan, Yong
    Peng, Jiang
    Ye, Kaiqi
    Xue, Pengchong
    Lu, Ran
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (39) : 6814 - 6823
  • [6] Synthesis and photophysical properties of pyrene-based green fluorescent dyes: butterfly-shaped architectures
    Vanga, Devendar Goud
    Santra, Mithun
    Keerthi, Ashok
    Valiyaveettil, Suresh
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (40) : 7914 - 7918
  • [7] Synthesis, Characterization, and Photophysical Properties of Novel Poly(p-phenylene vinylene) Derivatives with Conjugated Thiophene as Side Chains
    Ding, Tianpeng
    Zhao, Bin
    Shen, Ping
    Lu, Junjian
    Li, Hui
    Tan, Songting
    JOURNAL OF APPLIED POLYMER SCIENCE, 2011, 120 (06) : 3387 - 3394
  • [8] Synthesis and Photophysical Properties of Pyrene-Based Light-Emitting Monomers: Highly Pure-Blue-Fluorescent, Cruciform-Shaped Architectures
    Hu, Jian-yong
    Era, Masanao
    Elsegood, Mark R. J.
    Yamato, Takehiko
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (01) : 72 - 79
  • [9] Thiophene-Based, Radial π-Conjugation: Synthesis, Structure, and Photophysical Properties of Cyclo-1,4-phenylene-2′,5′-thienylenes
    Ito, Hideto
    Mitamura, Yukari
    Segawa, Yasutomo
    Itami, Kenichiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (01) : 159 - 163
  • [10] Synthesis and photophysical properties of poly(p-phenylene vinylene) via ruthenium-based acyclic diene metathesis (ADMET) polymerization.
    Miller, CG
    Harper, AW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U539 - U539