Synthesis of Highly Soluble and Oxidatively Stable Tetraceno[2,3-<i>b</i>]thiophenes and Pentacenes
journal contribution
posted on 2007-08-17, 00:00 authored by Sujeewa
S. Palayangoda, Rajib Mondal, Bipin K. Shah, Douglas C. NeckersA comparative study of suitably functionalized, highly soluble
tetraceno[2,3-<i>b</i>]thiophenes (<b>1</b>−<b>3</b>) and pentacenes (<b>4</b>−<b>6</b>) that
show higher photoxidative stability than that of unfunctionalized
corresponding acenes is reported. The absorption and emission of <b>1</b>−<b>3</b> (<i>A</i><sub>max</sub> =
624−656 nm, λ<sub>max</sub> = 634−672 nm, Φ<sub>F</sub> ≈ 10%) and <b>4</b>−<b>6</b> (<i>A</i><sub>max</sub> = 672−704 nm, λ<sub>max</sub> = 682−718 nm, Φ<sub>F</sub> ≈ 10%) were found
to be systematically red-shifted by the substitution in the order
of the <i>tert</i>-butylethynyl < triisopropylsilylethynyl
< phenylethynyl groups. The oxidation potentials of these compounds
were similar (<i>E</i><sub>1/2</sub> ≈ 0.70 V), except
for <b>4</b>, which showed lower oxidation potential (<i>E</i><sub>1/2</sub> ≈ 0.63 V).
History
Related Materials
- 1. DOI - Is supplement to Synthesis of Highly Soluble and Oxidatively Stable Tetraceno[2,3-b]thiophenes and Pentacenes
