Pro-aromatic quinoidal compounds possess unique optical, electronic and magnetic properties due to their narrow bandgaps and diradical contribution in the ground state. A series of ladder-type quinoidal small molecules, oligomers and polymers derived from quinacridone was synthesized and investigated. Small bond length alternation of quinoidal structures and low torsional angles of ladder-type backbones leads to narrow bandgaps in this system. Both elongation of ladder-type backbones and various ratios of quinoidal/aromatic building blocks have correlated influences on properties related to energy levels and diradical characters. Besides, different aggregation behavior induced by structural variation and acid doping of this aniline-like structure also promote bandgap engineering. Structure-property relationship was established in this study, serving as a general guideline for molecular design with desired energy levels and band gaps for opto-electronic applications.

Structure-property correlation study of quinoidal ladder oligomers and polymers

253rd National Meeting (2017)

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