Acid-Mediated Dimerization of TIPS-Pentacene
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 .
Fields of Study & Subjects
Organic Electronics and Photovoltaics
Synthesis and Properties of Aromatic Compounds
Organic Light-Emitting Diodes Research
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 4
- Pages
- 1842–1847
- Publication date
- 20 January 2026
- Language
- EN