Open AccessEffect of Internal BN Substitution on Electronic Properties of Pyrene Derivatives
Author(s) -
Li An
Publication year - 2019
Publication title -
iop conference series. materials science and engineering
Language(s) - English
Resource type - Journals
eISSN - 1757-899X
pISSN - 1757-8981
DOI - 10.1088/1757-899x/689/1/012009
Subject(s) - pyrene , delocalized electron , dipole , chemistry , density functional theory , photochemistry , computational chemistry , excited state , chemical physics , excimer , transition dipole moment , atomic physics , organic chemistry , fluorescence , physics , quantum mechanics
Pyrene as an important chemical building block has found wide applications in the field of organic electronics. In solution, pyrene and its derivatives are well-known examples for excimer formation. Here, we studied the boron-nitrogen (BN)-substituted pyrene, decorated with thiophene side chain. From density-functional theory (DFT) calculation, this isoelectronic BN substitution maintains the coplanarity of the central motif and the delocalized π-electron distribution, but additionally induces a much stronger permanent dipole moment. Time-dependent DFT indicates a much-reduced oscillator strength for low energy transitions, and surprisingly a forbidden π-π* transition, therefore resulting in a much red-shifted absorption spectrum. Our simulation results call for future experiments to study the photo-excited properties of BN-substituted pyrene and molecular self-assembly through dipole-dipole interaction and π-π* interaction.