Synthesis of Cyclotriveratrylene-Phenylacetylene Derivatives and a Photophysical Investigation of Rigid Conjugated Cyclotriveratrylene Dendrimers

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‐I3 derivatives 3a and 3b and their Sonogashira cross‐coupling with various terminal aryl‐alkynes, to synthesize CTV‐phenylacetyl...

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Bibliographic Details
Published in:European journal of organic chemistry 2012-12, Vol.2012 (35), p.6895-6903
Main Authors: Han, Xiao-Na, Chen, Jian-Ming, Huang, Zhi-Tang, Zheng, Qi-Yu
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Applied sciences
Chemistry
Cross-coupling
Dendrimers
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Macrocycles
Molecular modeling
Organic chemistry
Organic polymers
Physicochemistry of polymers
Polymers with particular structures
Preparation, kinetics, thermodynamics, mechanism and catalysts
Preparations and properties
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Summary: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‐I3 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. Cyclotriveratrylene (CTV) was functionalized by Sonogashira cross‐coupling of CTV‐I3 with a range of aryl‐substituted alkynes. Among these novel macrocyclic derivatives, three star‐like conjugated dendrimers with rigid macrocyclic cores display excellent photophysical properties.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201201024