Hydrophobic-lipophilic interaction (HLI) is one of the most important non-covalent interactions. Aggregation and self-coiling of organic molecules in polar solvent media are mainly promoted by HLI. In the past twenty years, we have studied HLI-driven aggregation and self-coiling of a variety of organic molecules, which include linear aliphatic and aromatic carboxylates, sulfonates, phosphates, aromatic and heterocyclic systems, etc. Factors which affect the aggregating and self-coiling tendencies of organic molecules have been systematically investigated. These include solvent effects, salt effects, structural effects such as molecular shape, linked - up effect, chain-length effect, the alternating -CF~2CH~2- chain effect, the hydroxyl - group effect, a special salt effect for ESAg formation, etc. Our efforts have led to the establishment of a number of new concepts, e. g. , coaggregation, deaggregation, electrostatically stabilized aggregation, neighboring-moiety-assisted chain-foldability effect, etc. The results have also been successfully applied to various reactions such as HLI-driven electron transfer, energy transfer and large-ring synthesis and to a partial interpretation of why some molecules are the culprits of atherosclerosis. This paper briefly describes our main research results.

Key words: HYDROPHOBILITY, LIPOPHILICITY, INTERACTIONS