Hexaarylbiimidazoles(HABI)-functionalized lyotropic liquid crystalline systems as visible light-responsive materials

• Published in: Journal of colloid and interface science Vol. 579; pp. 379 - 390
• Main Authors: Jia, Shiyang, Graham, Bim, Capuano, Ben, Tan, Angel, Hawley, Adrian, Boyd, Ben J.
• Format: Journal Article
• Language: English
• Published: Elsevier Inc 01.11.2020
• Subjects: Drug delivery; Hexaarylbiimidazoles; Liquid crystal; Visible light-responsive; Visible light-responsive; Hexaarylbiimidazoles; Drug delivery; Liquid crystal
• ISSN: 0021-9797; 1095-7103
• DOI: 10.1016/j.jcis.2020.06.006

[Display omitted] Hexaarylbiimidazoles (HABIs) are a promising class of photoswitchable molecule that have received little attention in the literature. Among them, (2,2′-dimethoxydiphenylimidazole)-1,1′-binaphthyl (HABI1) displays unusual negative photochromism and is responsive to green light. This study investigates the potential of HABIs to serve as photo-responsive actuators controlling the structure of lyotropic liquid crystalline (LLC) materials. HABI1 with four methyl chains and HABI2 with four dodecyl chains were synthesized. Time resolved small angle X-ray scattering was used to characterize the potential disruptive effects of HABIs on the nanostructure of LLC systems. HABIs underwent rapid isomerization under irradiation, with a very slow reversion in the dark in toluene and in the LLC matrix, demonstrating excellent stability and photo-fatigue resistant. HABIs completely triggered phase transitions in the phytantriol-based materials, and HABI2 generated a greater disruption than HABI1 on the lipid packing due to the enhanced steric influence. Tuning the lipid composition yielded systems that transitioned from a “slow release” lamellar phase to a “burst release” bicontinuous cubic phase upon light irradiation. Such systems therefore may exhibit a triggered release behavior upon a short time of irradiation, showing great potential in “on demand” drug delivery.