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Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons
Author(s) -
Miletić Tanja,
Fermi Andrea,
Orfanos Ioannis,
Avramopoulos Aggelos,
De Leo Federica,
Demitri Nicola,
Bergamini Giacomo,
Ceroni Paola,
Papadopoulos Manthos G.,
Couris Stelios,
Bonifazi Davide
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604866
Subject(s) - intramolecular force , hyperpolarizability , homo/lumo , annulation , absorption (acoustics) , photochemistry , chemistry , absorption spectroscopy , materials science , molecule , organic chemistry , optics , catalysis , physics , polarizability , composite material
The synthesis of O‐doped polyaromatic hydro‐ carbons in which two polycyclic aromatic hydrocarbon sub units are bridged through one or two O atoms has been achieved. This includes high‐yield ring‐closure key steps that, depending on the reaction conditions, result in the formation of furanyl or pyranopyranyl linkages through intramolecular C−O bond formation. Comprehensive photophysical measurements in solution showed that these compounds have exceptionally high emission yields and tunable absorption properties throughout the UV/Vis spectral region. Electrochemical investigations showed that in all cases O annulation increases the electron‐donor capabilities by raising the HOMO energy level, whereas the LUMO energy level is less affected. Moreover, third‐order nonlinear optical (NLO) measurements on solutions or thin films containing the dyes showed very good values of the second hyperpolarizability. Importantly, poly(methyl methacrylate) films containing the pyranopyranyl derivatives exhibited weak linear absorption and NLO absorption compared to the nonlinearity and NLO refraction, respectively, and thus revealed them to be exceptional organic materials for photonic devices.