Effect of symmetric and asymmetric substitution on the optoelectronic properties of 9,10-dicyanoanthracene

Abstract

Six newly synthesised 9,10-dicyanoanthracene derivatives exhibit high two-photon absorption cross sections particularly upon symmetric substitution with strong electron donors.

Excited-state symmetry breaking in 9,10-dicyanoanthracene-based quadrupolar molecules: the effect of donor–acceptor branch length

“…According to quantum-chemical calculations, the first oneand two-photon absorption bands correspond to the S 1 ←S 0 and S 3 ←S 0 transitions, respectively. 42,43 Table 1 reveals that, although the V ib values deduced from these calculated excitation energies are larger than those determined from the measured spectra, they also decrease with increasing the D-A branch length.…”

“…Estimated inter-branch coupling, V ib , and solvation energies of the dipolar state in BCN, E s,D (BCN), expressed in cm −1 .ν TPA : wavenumber of the first two-photon allowed absorption band;ν OPA : wavenumber of the first one-photon allowed absorption band; E S 1 and E S 3 : energies of the first and third excited states taken from ref 43. …”

Toward an understanding of electronic excitation energies beyond the molecular orbital picture

“…[63][64][65][66] A particular effort has been devoted to the task of visualising excited-state correlations using either correlation plots [67][68][69][70][71][72] or a newly developed technique for visualising correlation effects in real space. 36 The availability of the tools discussed above can have a substantial impact on applied studies not only through quantifying excited-state character 9,73,74 but also through providing new insight into intricate wavefunction properties that would otherwise be hard to come by. 31,75 However, so far wavefunction analysis is usually restricted to characterising excited states within pre-existing models based mostly on the MO picture.…”

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

“…our recently developed method for the synthesis of substituted 9,10-anthracenedicarbonitriles (also known as 9,10dicyanoanthracenes). [10][11][12][13][14] However, as with our method, most available synthetic methods yield anthracene derivatives with substituents in the central 9-and 10-positions. The preparation of anthracene derivatives without substituents in these positions is often more challenging.…”