Dibenzocycloocta-1,5-diene (DBCOD) consists of eight-membered cycloalkane ring stabilized by fusing two benzene rings. This rigid-flexible-rigid organic moiety undergoes conformational change, <i>i.e.,</i> from Boat to Chair. This intrinsic property can render a reversible molecularly switchable system that can be actuated by low-energy stimuli. The distinct switching mechanism is complimentary to existing systems such as the azobenzene cis-trans isomerization which requires higher energy stimuli. In this talk, we present the synthetic methods to prepare DBCODs with substitutions to modulate intramolecular interaction (H-bonding or π-π stacking) which in turn influences the DBCOD conformational dynamics. The effect of substitution on thermodynamics and kinetics of the conformational change will be discussed. This work has laid the basis to construct systems for low-energy driven stimuli-responsive applications, hitherto a challenge to overcome. The potential of harnessing the controlled conformational change for stimuli responsive optoelectronic materials is being investigated, through appending conjugated π-systems

Tailoring substituents of dibenzocycloocta-1,5-diene towards stimuli responsive materials

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ACS Fall 2022

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