engleski

Phenathridine – Nucleobase Conjugates: Supramolecular pH-dependent Fluorescent Hydrogelators

Numerous small organic molecules self-organize to form gels by spontaneous and reversible self- assembly.Gel-to-sol transitions can be controlled and induced by temperature, pH, light, ultrasound, or a specific solute. Steric and electronic properties of gelator molecules determine both type and direction of inter- and intramolecular non-covalent interaction, and thereby structure of gel, its properties and functions. Small molecules containing nucleobase moiety showed gel formation that was caused by H-bond formation between nucleobases. Introduction of fluorophoremoiety introduces aditional functionalisation of gelator: aggregation - induced emission enhancement properties – AIEE. This gel property can be used for design and developement of new functional fluorescent materials, e.g. for biosensors and chemosensors. New phenanthridine – adenine conjugates were prepared in order to study the influence of the linker length to the intramolecular conformation, self-association in water and gel properties. Phenanthridine – adenine conjugates DA-3 and DA-5 showed self-aggregation and gel- formation in acidic water solution. Self- aggregation was probably caused by inter-and intramolecular - aromatic stacking interactions of aromatic subunits and H-bonding between protonated adenines.

Phenanthridine ; Nuclobase ; Hydrogelator ; Self-aggregation

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