Organometallic rubidium and cesium compounds of the 5,6;11,12-di-o-phenylene-tetracene dianion

Abstract

Twofold reduction of the title molecule 5,6;11,12-di-o-phenylenetetracene (DOPT) with an excess of metallic rubidium and cesium in the presence of strongly coordinating ethers like 18-crown-6-ether (18C6) and tetraglyme results in the formation of the first Rb(i) triple-decker complex and the first Cs(i) coordination polymer of the so far only sparsely studied polyaromatic planar hydrocarbon DOPT. Both compounds are extremely sensitive towards air and water in solution as well as in the solid state. Both compounds exhibit isomerism within their crystal lattices.

Geodesic‐Planar Conjugates: Substituted Buckybowls—Synthesis, Photoluminescence and Electrochemistry

“…Geodesic polyarenes are well known for their ability to be reduced by one or more electrons. Several studies were devoted to examining their electrochemical properties as well as the structures of the corresponding reduced forms as their alkali and alkaline earth salts [22, 46] . Whereas CA can be reversibly reduced by up to four electrons, indacenopicene only displays two reversible one‐electron reductions.…”

“…Several studies were devoted to examining their electrochemical properties as well as the structures of the corresponding reduced forms as their alkali and alkaline earth salts. [22,46] Whereas CA can be reversibly reduced by up to four electrons, indacenopicene only displays two reversible one-electronr eductions. This is the consequenceo ft he symmetry lowering from C 5v to C S and the concomitantlifting of the degeneracy of the first two lowest unoccupied molecular orbitals.…”

Unveiling the Multielectron Acceptor Properties of π-Expanded Pyracylene: Reversible Boat to Chair Conversion

“…Similar bond length alterations were observed for the doubly reduced products of phenylenetetracene and indenocorannulene. 68,47 The bond lengths of a and d become smaller and more equalized (1.43/1.38 Å in 1 vs 1.39/1.37 Å in 1 − and 1.38/1.35 Å in 1 2− ). In contrast, the C−C bonds b and c are slightly elongated and cover a broader range (Table 1).…”

Reduced Knoevenagel Reaction of Acetetracenylene-1,2-dione with Acceptor Units for Luminescent Tetracene Derivatives

“…Functionalization of tetracene is an intriguing subject because it has greater stability during handling than pentacene and is less well explored than anthracene in terms of derivatization. Modification of tetracene has been investigated for π-system expansion to nanographenes and fused π-systems, construction of fused donor–acceptor systems for light harvesting, and other purposes . Expected applications of tetracene derivatives include charge carrier transport materials, organic solar cells, and singlet fission .…”