Synthesis, Optical Properties, and Crystal Structure of 1,4‐Dipropyltetracene

Abstract

We synthesized 1,4-dipropyltetracene on a 200-mg scale, the key step of which involved a Diels-Alder reaction between alkyl-substituted o-quinodimethane, generated in situ, and 1,4-naphthoquinone. The product was obtained as an orange solid, which was soluble in organic solvents including hexane. The optical properties of the product in solution showed no marked differences from those of other 1,4,7,10-tetraalkyltetracenes. Solid-state absorption and fluorescence spectra

Near-Infrared Solid-State Emitters Based on Isophorone: Synthesis, Crystal Structure and Spectroscopic Properties.

“…With few exceptions, organic red or near-infrared emitting fluorophores , are flat molecules with extended π-conjugation or strong dipolar donor−acceptor push−pull molecules and therefore prone to aggregation and fluorescence quenching in the solid-state. The most obvious way to restore the fluorescence is to prevent the molecular packing or the π−π-stacking by introducing bulky spacer groups at the periphery of the fluorophores . This approach has proved successful even for molecules with small Stokes shifts such as BODIPY .…”

Tris(tetraceno)triquinacenes: Synthesis and Photophysical Properties of Threefold Linearly Extended Tribenzotriquinacenes

“…The efficient threefold extension of the TBTQ framework in the case of compound 8 allowed us to synthesize the tris(tetraceno)triquinacene hydrocarbons 9 and 10 (Scheme ). Quinone 8 was reduced to the corresponding threefold 5,12‐dihydrotetracene‐5,12‐diol by the use of sodium borohydride in THF/methanol 20d. The hexa‐alcohol was not isolated in pure form but reduced further with stannous chloride in aqueous hydrochloric acid7a to give tris(2,3‐tetraceno)triquinacene 9 as a yellow/orange solid in a remarkably good yield.…”