Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202301476
Keywords
cations; electrochromic materials; multi-electron redox systems; NIR absorptions; X-ray diffraction
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By synthesizing new octakis(aminophenyl)-substituted pentacenebisquinodimethane (BQD) derivatives and their hybrids with alkoxyphenyl analogues, the study successfully generated and isolated dicationic and tetracationic states with apparent two-electron transfer, minimizing the involvement of open-shell species. This achievement allows for the development of multi-color electrochromic systems with improved reversibility.
Most redox systems generally cannot avoid the involvement of open-shell species upon generating multiply charged species, which often reduces reversibility in multi-color electrochromic systems. In this study, we newly synthesized octakis(aminophenyl)-substituted pentacenebisquinodimethane (BQD) derivatives and their hybrids with alkoxyphenyl analogues. Thanks to apparent two-electron transfer accompanied by double dramatic changes in the structure of the arylated quinodimethane skeleton, the dicationic and tetracationic states were generated and isolated quantitatively because of the negligible steady-state concentration of intermediary open-shell species such as monocation or trication radicals. When two electrophores with different donating abilities are attached to the BQD skeleton, a dicationic state with a different color can be isolated in addition to the neutral and tetracationic states. For these tetracations, an interchromophore interaction induces a red-shift of the NIR absorptions, thus realizing tricolor UV/Vis/NIR electrochromic behavior involving only closed-shell states.
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