Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 17, Pages 6127-6132Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob05508a
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Aseries of six new, highly soluble N,N'-dialkylated isoindigo derivatives bearing different electron donating thiophene units at the 6,6'-positions were synthesized by Stille cross-coupling reaction. The optical and electrochemical properties of these dyes were studied by UV-vis spectroscopy and cyclic voltammetry, revealing a good tunability of their electronic properties by peripheral substituents with amino groups leading to strong absorption reaching the NIR region. The DFT calculations of the frontier molecular orbitals of these dyes corroborate the observed substituent effect on absorption and redox properties.
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