We recently synthesized a large variety of functionalized pentacenes with HOMO-LUMO gaps at or below 2 eV.  Of all the derivatives examined, we find that 6,13-bis(organothio)pentacenes are amongst the most soluble in hydrophobic solvents (e.g., hexanes, chloroform, methylene chloride, toluene, etc.) and the most resistant to photooxidation. These characteristics make 6,13-bis(organothio)pentacenes attractive for thin-film electronic device construction using standard techniques such as spin coating, blade coating or spray coating. Typically, such devices require multi-layer constructions in which successive thin-films are deposited from solvents of complementary polarity.  Thus, a water soluble organic semiconductor would typically be deposited atop an organic soluble organic semiconductor and vice versa. For this reason, pentacene derivatives that are soluble in hydrophilic solvents, especially those bearing 6,13-bis(organothio) functionality, are much desired.  In this presentation, I will discuss the synthesis, isolation and characterization of the first water-soluble pentacene (WSP) derivative.                                                             

First water-soluble pentacene derivative

244th National Meeting (2012)

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