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A DNA-encoded chemical library (DECL) is built with combinatorial chemistry, which works by bringing chemical fragments together to generate diverse structures. However, chemical diversity of DNA-encoded chemical libraries is often limited by DNA compatible synthetic reactions. This report shows a conceptual strategy to expand chemical space of DNA-encoded chemical libraries by incorporation of diversity-oriented synthesis in DECL synthesis. We developed Aldol reactions on DNA in a combinatorial way. After obtaining DNA-tagged α, βunsaturated ketones which represent important chemical intermediates, many distinct structures with skeletal diversities are achieved by diversity-oriented synthesis.

A group of novel sugar‐based gemini surfactants, N, N′‐bis(2‐hydroxy‐3‐alkyloxylpropyl) ‐N, N′‐bis(gluconylamide)‐ethylenediamine (alkyl: n‐C8H17, n‐C12H25, n‐C14H29, n‐C16H33), were synthesized and characterized. Their surface properties, including surface tension, γ, critical micelle concentration, CMC, maximum surface excess, Гmax, minimum area per molecule, Amin, and standard free energy of micellization and adsorption, normalΔGm0 and normalΔGads0, were investigated. The members of this family could reduce the surface tension of water to approximately 20–25 mN m−1 at the concentration level of 10−5 mol L−1, considerably lower than that commonly achieved with monomeric surfactants. Their adsorption and aggregation behavior were further studied by means of dynamic light scattering and X‐ray diffraction. The relationship of the aggregate size of the synthesized gemini surfactants with the length of the hydrocarbon chain and their concentration was discussed.

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