Rational design of long-wavelength absorbing and emitting carbostyrils aided by time-dependent density functional calculations

摘要: Abstract We have used computational chemistry methods to aid the rational design of long-wavelength absorbing and emitting organic materials. For this purpose, vertical electronic transition energies 3,4-dicyano carbostyrils (quinolone-2(1H)-ones) substituted by electron-donating substituents (methoxy, methylamino, dimethylamino) at positions 6 7, are calculated time-dependent density functional theory (B3LYP) within Tamm–Dancoff approximation. Bulk solvent effects (DMSO, CH 3 CN, H 2 O) were taken into account CPCM solvation model. Particular absorptions (∼540 nm) predicted for derivatives containing an amino group in position irrespective whether a 7-methoxy or 7-amino is present. In contrast, considerably shorter wavelength absorption (∼440 nm) can be expected 6-methoxy-7-amino carbostyrils. Optimization first excited singlet state 6-dimethylamino leads perpendicular arrangement (CH ) N-group with respect heterocyclic ring system accompanied extremely low energy (1000–1500 nm) vanishingly small intensity (oscillator strength f