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).