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Synthesis of Cyclotriveratrylene–Phenylacetylene Derivatives and a Photophysical Investigation of Rigid Conjugated Cyclotriveratrylene Dendrimers
Author(s) -
Han XiaoNa,
Chen JianMing,
Huang ZhiTang,
Zheng QiYu
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201024
Subject(s) - chemistry , dendrimer , phenylacetylene , conjugated system , stereochemistry , organic chemistry , polymer , catalysis
Various functionalized host molecules and building blocks can be derived from the cone‐shaped cyclotriveratrylene (CTV). In this article, we report on the synthesis of CTV‐I 3 derivatives 3a and 3b and their Sonogashira cross‐coupling with various terminal aryl‐alkynes, to synthesize CTV‐phenylacetylene derivatives in moderate to good yields. In this way, three star‐like conjugated dendrimers with rigid macrocyclic cores 4k – m , which showed good photophysical properties, were also synthesized. The band gaps of 4k – m are 3.49, 3.49 and 3.45 eV, and the fluorescence quantum yields are 0.64, 0.78, 0.48 (2‐aminopyridine as a standard and excited at 310 nm), respectively. Electrochemical studies revealed their HOMO and LUMO energy levels. Our research disclosed that these CTV dendrimers could potentially be used as host materials in OLEDs.