Synthesis and Properties of Carborane-Appended C3-Symmetrical Extended π Systems
Top Cited Papers
- 16 April 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (18), 6578-6587
- https://doi.org/10.1021/ja101845m
Abstract
A series of C(3)-symmetric pi-conjugated compounds containing three to six o-carborane clusters have been synthesized by employing palladium-catalyzed Suzuki coupling reactions and palladium-catalyzed acetylation reactions, followed by silicon tetrachloride mediated trimerization reactions. Carborane-containing extended trimers were found to emit blue light. Incorporation of o-carborane clusters into extended pi-conjugated systems led to 22-70% enhancement of their relative fluorescence quantum yields. Decapitation of o-carborane clusters made these extended trimers water soluble, and their aqueous solutions were also found to be fluorescent, but with a reduced fluorescence intensity. The carborane-appended pi-conjugated compounds are found to be extremely thermally stable, and for some of these compounds only 10% mass loss occurred at temperatures close to 500 degrees C. The DSC thermograms of smaller C(cage)-appended trimers indicate the occurrence of solid-solid phase transitions.Keywords
This publication has 94 references indexed in Scilit:
- Stoichiometric Control of Multiple Different Tectons in Coordination-Driven Self-Assembly: Preparation of Fused Metallacyclic PolygonsJournal of the American Chemical Society, 2009
- Multicomponent Supramolecular Systems: Self‐Organization in Coordination‐Driven Self‐AssemblyChemistry – A European Journal, 2009
- Self-Organization in Coordination-Driven Self-AssemblyAccounts of Chemical Research, 2009
- Soluble Polymer Carriers for the Treatment of Cancer: The Importance of Molecular ArchitectureAccounts of Chemical Research, 2009
- Construction of Multifunctional Cuboctahedra via Coordination-Driven Self-AssemblyJournal of the American Chemical Society, 2009
- Biodegradable dendritic positron-emitting nanoprobes for the noninvasive imaging of angiogenesisProceedings of the National Academy of Sciences of the United States of America, 2009
- Surface Confined Metallosupramolecular Architectures: Formation and Scanning Tunneling Microscopy CharacterizationAccounts of Chemical Research, 2008
- Coordination-driven self-assembly of functionalized supramolecular metallacyclesChemical Communications, 2008
- Enhanced aqueous solubility of long wavelength voltage-sensitive dyes by covalent attachment of polyethylene glycolOrganic & Biomolecular Chemistry, 2007
- Poly[di(2-thiophenyl)carborane]s: conducting polymers with high electrochemical and thermal resistanceChemical Communications, 2007