Abstract
A series of benzo[ghi]perylene (Bp) and coronene (Cor) derivatives substituted with electron-withdrawing methoxycarbonyl (COOMe) or electron-donating methoxyl (MeO) groups was synthesized. The electrochemical, spectroscopic, and photophysical properties of these compounds were investigated by cyclic voltammetry, steady-state and time-resolved spectroscopy, and quantum-yield measurements. Introduction of suitable substituents onto the aromatic rings enabled control of electrochemical and spectroscopic behavior. Examination of excited-state dynamics revealed that fluorescence quantum yields increased with increasing number of COOMe groups in both Bp and Cor derivatives, consistent with the findings of DFT calculations. Single-crystal analysis allowed the performance of field-effect transistors containing single crystals of the derivatives to be rationalized. Crown decoration: A series of benzo[ghi]perylene and coronene derivatives decorated with different numbers of electron-donating or electron-withdrawing substituents was synthesized in order to control their fluorescence quantum yields and carrier-transport properties (see figure).
Original language | English |
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Pages (from-to) | 9081-9093 |
Number of pages | 13 |
Journal | Chemistry - A European Journal |
Volume | 20 |
Issue number | 29 |
DOIs | |
Publication status | Published - 2014 Jul 14 |
Keywords
- device fabrication
- electrochemistry
- fluorescence
- polycycles
- solid-state structures