Pyrazine-Containing Acene-Type Molecular Ribbons with up to 16 Rectilinearly Arranged Fused Aromatic Rings
Citations Over TimeTop 10% of 2008 papers
Abstract
A series of acene-type conjugated molecules (1-5) containing 2-6 pyrazine units and up to 16 rectilinearly arranged fused aromatic rings were synthesized by condensation coupling of 1,2-diamines and 1,2-diketones. The energy gap of the molecules estimated from absorption edge decreases with an increase in molecular length, indicating the well-delocalized nature of the molecules. The cyclic voltammetry measurements suggest that the n-type properties of these ribbonlike pyrazine derivatives are dependent on the molecular length and the number of the pyrazine units. As the number of pyrazine units and the molecular length increase, the first reduction wave onset is shifted from -1.16 to -0.62 V (vs Ag/AgCl), corresponding to the LUMO energy levels of -3.24 and -3.78 eV, respectively. These molecules tend to aggregate in solution more readily with an increase in molecular length, as evident by (1)H NMR and UV-vis absorption spectra. Introduction of t-butyl groups in pyrene units can noticeably suppress the aggregation of these molecules in solution. High electron affinity, high environmental stability, and ease of structural modification make these compounds excellent candidates as a new class of n-type semiconductors.
Related Papers
- → n‐Type Azaacenes Containing B←N Units(2017)94 cited
- → Observation of d–p hybridized aromaticity in lanthanum-doped boron clusters(2013)51 cited
- → n‐Type Azaacenes Containing B←N Units(2017)22 cited
- → Tunable spectroscopic and electrochemical properties of conjugated push–push, push–pull and pull–pull thiopheno azomethines(2007)74 cited
- → A density functional theory investigation of the stability, aromaticity, and photophysical behavior for the highly conjugated macrocycles containing 4 pyrroles(2016)3 cited