Donor–Acceptor Molecular Triangles

Abstract

The synthesis and optoelectronic properties of five donoracceptor molecules, featuring an electron-acceptor unit made of six fused benzenoid rings that resembles an equilateral triangle, are described. These molecular 'triangles' were synthesized in eight steps from simple building blocks such that the electron-donor substituents could be installed in the last step by means of the Suzuki cross-coupling reaction. All molecules absorb and emit visible light in the region of around 450-650 and 550-850 nm, respectively, exhibit solvatochromism, and possess up to four redox states.

Gram-Scale Synthesis and Supramolecular Complex of Precursors of Clar’s Hydrocarbon Triangulene

“…We showed that the tri- tert -butyl derivative of 2 can easily be converted into donor–acceptor dyads with rare layered solid-state packing motifs. 7 Finally, because of the extra stabilization provided by the peripheral oxygen atoms, the doubly reduced conjugate base of 2 was the first TOT derivative with a triplet ground state detected by EPR spectroscopy. 8…”

Synthesis of Trioxotriangulene Stable Neutral π-Radicals Having Alkyl Substituent Groups, and Their Effects on Electronic-spin and π-Stacking Structures

“…10 Recently, several efficient methods for synthesizing TOT precursors were reported, however, further chemical modifications of the neutral radicals were not investigated. 11,12 In this study, we have newly synthesized TOT derivatives 1e and 1f having isopropyl and n-butyl groups, respectively, and investigated the steric effect of substituent groups on the π-stacking ability. The isopropyl group is sterically smaller than the tert-butyl group, and the n-butyl group is linear and more flexible.…”