Electronic Structures and Spectra of a Novel Diquinone; 1,4 : 5,8-Anthracenediquinone

Abstract

Assignment of the electronic absorption spectrum of 1,4 : 5,8-anthracenediquinone (1,4 : 5,8-ADQ) has been carried out with the aid of magnetic circular dichroism and LCAO MO SCF CI calculations including all valence electrons. The lowest energy absorption region of 1,4 : 5,8-ADQ has been revealed to be composed of the n-π* transition or transitions. The higher energy absorption region has been concluded to consist of four π-π* transitions, which are regarded as Lb, La, Ba, and Bb in the Platt’s notation for anthracene. The above assignment of 1,4 : 5,8-ADQ has been experimentally confirmed with its linear dichroism spectra in stretched polyethylene sheets and its circular dichroism spectra in the β-cyclodextrin solution. The relationship between the absorption spectra of 1,4 : 5,8-ADQ and 1,4-naphthoquinone has been discussed from the experimental and theoretical points of view.

A linear dichroism study of the 1,4-naphthoquinone chromophore

“…The former polarisation corresponds to benzenoid, the latter to quinonoid x -7c * transitions (if a polarisation perpendicular to the molecular plane is not considered), in agreement with that reported in ref. 11 and with previous assignments. '-* (11).…”

“…11 and with previous assignments. '-* (11). The absorption spectrum of (11) shows a new structured band at ca.…”

Magnetic circular dichroism within the Algebraic Diagrammatic Construction scheme of the polarisation propagator up to third order

“…77 These results have earlier provided a reference for theoretical investigations at different levels of theory. 18,23,32,[76][77][78] A TD-DFT study, 18 in particular, showed contradictory results with respect to the experimental data, which makes NQ and AQ interesting test cases for our MCD-ADC scheme. Given the size of NQ and AQ, only RICC2 and ADC(2) are considered.…”

Synthesis of 1,2,5,6- and 1,4,5,8-anthracenetetrone: Building blocks for π-conjugated small molecules and polymers

“…[23] The absorption and electrochemical properties of this tetrone, which is the most stable anthracenetetrone according to a computational study, [24] were reported decades ago. [11,25] In a more recent study, the binding of this tetrone on graphene was computationally predicted to be the strongest of several electroactive compounds for green battery electrodes. [26] Such strong binding benefits the cycling performance of batteries.…”