Halogen Effect on Non‐Conventional Organogel Assisted by Balanced π‐π Interaction. Issue 19 (4th July 2017)

• Record Type: Journal Article
• Authors: Li, Qian; Li, Ruohan; Lan, Haichuang; Lu, Yunxiang; Li, Yaqian; Xiao, Shuzhang; Yi, Tao
• Is Part Of: ChemistrySelect. Volume 2:Issue 19(2017)
• Page Start: 5421
• Page End: 5426
• Publication Date: 2017-07-04
• Subjects: Fluorescence -- halogen effect -- non-conventional -- organogel -- π-π interaction; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201700760
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Triphenylamine‐functionalized anthracene derivatives bearing no alkyl chains or amide units (ADIPA andBr‐ADIPA ) are synthesized in a straightforward manner. Among these two compounds, Br‐ADIPA could form stable gel in organic solvents, butADIPA cannot gelate any conventional solvents under the tested conditions. In order to disclose the supramolecular self‐assembly ofBr‐ADIPA gel, a series of characterizations were performed, which indicated that it might self‐assemble into aggregates which do not involve π‐π stacking between anthracene chromophore in the gel state, and intermolecular π‐π interactions between phenyl rings on triphenylamine moieties are essential driven forces for its gelation. Interestingly, the self‐assemblies of these two compounds calculated using Polymorph software well matched the characterization results. It revealed that a one‐dimensional molecular packing was promoted by multiple intermolecular π‐π interactions between triphenylamine units inBr‐ADIPA, and the bromine atom played important role in its balanced intermolecular π‐π interactions. In comparison, these supramolecular forces inADIPA provided a three‐dimensional structure. Abstract : A triphenylamine‐functionalized anthracene derivative bearing no alkyl chains or amide units could form stable gel in organic solvents. The intermolecular π‐π interactions between triphenylamine units play important roles in its one‐dimensional self‐assembly and is ascribed to be the main driven force for gelation, however, the halogen atom is found to be an auxiliary group to promote the balanced intermolecular π‐π interactions.