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The Effect of Protonation on the Optical Properties of Conjugated Fluorene–Pyridine Copolymers
Author(s) -
Kappaun Stefan,
Horner Stephan,
Kelterer AnneMarie,
Waich Kerstin,
Grasse Florian,
Graf Michael,
Romaner Lorenz,
Niedermair Fabian,
Müllen Klaus,
Grimsdale Andrew C.,
Saf Robert,
List Emil J. W.,
Zojer Egbert,
Slugovc Christian
Publication year - 2008
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200800386
Subject(s) - fluorene , protonation , luminescence , conjugated system , pyridine , photochemistry , chemistry , copolymer , spectroscopy , intersystem crossing , absorption (acoustics) , absorption spectroscopy , polymer chemistry , polymer , materials science , organic chemistry , excited state , optoelectronics , physics , ion , quantum mechanics , nuclear physics , singlet state , composite material
A series of conjugated alternating and statistical copolymers of fluorene and pyridine are synthesized and characterized. The compounds under investigation, namely poly[2,7‐(9,9‐dihexylfluorenyl)‐ alt ‐(2,6‐pyridinyl)] and poly[2,7‐(9,9‐dihexylfluorenyl)‐ stat ‐(2,6‐pyridinyl)], are prepared by a Suzuki‐type cross‐coupling reaction starting from commercially available materials utilizing the recently described catalyst trans ‐bis(dicyclohexylamine) palladiumdiacetate (“DAPCy”). The target compounds are investigated by nuclear magnetic resonance and infrared spectroscopy, matrix‐assisted laser desorption ionization time‐of‐flight mass spectrometry, thermal analysis, UV–Vis absorption spectroscopy, and luminescence measurements in solution and in the solid state. Special emphasis is placed on studying the consequences of protonation on the photophysical properties of the described materials. Achieving a concise microscopic understanding of the effects of protonation on the absorption and luminescence characteristics is crucial for potential applications in, e.g., optical sensors. To that aim, the results of the systematic studies of the photophysical properties are explained by quantum mechanical calculations.