10.1021/jo0710331.s002
Sujeewa
S. Palayangoda
Sujeewa
S.
Palayangoda
Rajib Mondal
Rajib
Mondal
Bipin K. Shah
Bipin K.
Shah
Douglas C. Neckers
Douglas C.
Neckers
Synthesis of Highly Soluble
and Oxidatively Stable
Tetraceno[2,3-<i>b</i>]thiophenes and Pentacenes
American Chemical Society
2007
nm
Amax
oxidation
λ max
2007-08-17 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Highly_Soluble_and_Oxidatively_Stable_Tetraceno_2_3_i_b_i_thiophenes_and_Pentacenes/2990635
A 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).