Mechanistic investigation reveals cationic species' role in dimerization of TIPS-pentacene, suggesting new degradation pathways.
TIPS-pentacene (TIPS-Pc), a benchmark organic semiconductor, is shown to undergo acid-induced dimerization upon treatment with strong Brønsted acids such as TFA. Mechanistic investigation suggests that protonation at the central pentacene ring generates a cationic species that activates the adjacent alkyne toward [4+2] cycloaddition with a second TIPS-Pc molecule, forming a brown dimeric intermediate neutralized subsequently to dimer 1. Spectroscopic, isotopic, and computational studies support this pathway, revealing proton-induced dimerization as an unrecognized degradation route in TIPS-Pc. The crystal structure reveals a new polymorph of TIPS-Pc dimer.
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Sharma et al. (2025) studied this question.
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