Work

Acid-Mediated Dimerization of TIPS-Pentacene

Year: 2026

Type: article

Abstract: TIPS-pentacene ( TIPS-Pc ), a benchmark organic semiconductor, is shown to undergo acid-induced dimerization upon treatment with strong Bro̷nsted acids, such as trifluoroacetic acid (TFA). Mechanistic studies indicate that some acids oxidize the pentacene core to form a radical cation, which then engages a second neutral TIPS-Pc molecule in a radical-mediated [4 + 2] cycloaddition. Subsequent neutralization with triethylamine furnished isolated dimer 1 . Spectroscopic analysis, isotopic test, and DFT calculations converge on this pathway, revealing acid-triggered, radical-cation-driven dimerization as an unrecognized degradation mode of TIPS-Pc .

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c02409

Authors: Vishali Sharma, Paulina Bartos, Maja Morawiak, Przemysław Gaweł

Institutions: Institute of Organic Chemistry, Polish Academy of Sciences, University of Łódź

Language: English

Topic: Organic Electronics and Photovoltaics

Subfield: Electrical and Electronic Engineering

Field: Engineering

Domain: Physical Sciences

Open Access status: green

Funders: Narodowe Centrum Nauki, Narodowa Agencja Wymiany Akademickiej

Awards: G284474571, G6781002535