Methyl Cinnamate-Derived Fluorescent Rigid Organogels Based on Cooperative π–π Stacking and CO···π Interactions Instead of H‑Bonding and Alkyl Chains

• Published in: Langmuir 2015-05, Vol.31 (17), p.4916-4923
• Main Authors: Ma, Yuan, Ma, Hengchang, Yang, Zenming, Ma, Jun, Su, Yuhu, Li, Wenfeng, Lei, Ziqiang
• Format: Article
• Language: English
• ISSN: 0743-7463; 1520-5827
• DOI: 10.1021/acs.langmuir.5b00275

A new class of rigid low-molecular-mass organic gelators (LMOGs) was synthesized by McMurry and Heck reactions, and their gels and photophysical properties were investigated. The LMOGs lacked alkyl chain and H-bonding units and produced good gelation ability in selected mixed organic solvents facilitated by cooperative π–π stacking and CO···π interactions. Sensitive gel–sol transformation by molecular aggregation and disaggregation was easily achieved upon heating and cooling. H–H 2D NOESY and X-ray diffraction (XRD) patterns showed the π–π stacking and CO···π interactions between tiny methyl acrylate groups as “tails”. Importantly, this soft interaction model offers a useful tool for the future design and construction of supramolecular structures. At present, the LMOGs reported herein offer a sensitive gel-formation ability and aggregation-induced emission (AIE) property and thus have promising application potentials as functional soft matter in amorphous materials, photoelectric materials, and so on.