Diindeno‐Fused Corannulene‐Extended Tetrathiafulvalenes

Abstract

Two regioisomeric extended tetrathiafulvalenes (TTFs) incorporating diindeno‐fused corannulene spacers were synthesized from suitable dione precursors using Horner‐Wadsworth‐Emmons olefination reactions. Both compounds are strong chromophores with a longest‐wavelength absorption that exhibited some degree of charge‐transfer character as inferred from solvatochromic behaviors and frontier orbital calculations. The compounds underwent two reversible one‐electron oxidations and a quasi‐reversible third oxidation during cyclic voltammetry conditions. The mono‐ and dications had characteristic NIR absorptions and both were EPR active. The dications with potential diradicaloid characters underwent reactions when generated in bulk.