Abstract
The development of well-organized structures with high luminescent properties in the solid and aggregated states is of both scientific and technological interest due to their applications in nanotechnology. In this paper we described the synthesis of amphiphilic and dumbbell shaped AIE-active tetraphenylethylene (TPE) derivatives and studied their self-assembly with solvophobic control. Interestingly, both TPE derivatives form a 3D flower-shape supramolecular structure from THF/water solutions at varying water fractions. SEM microscopy was used to visualise step-wise growth of flower-shape assembly. TPE derivatives also show good mechanochromic properties which can be observed in the process of grinding, fuming and heating. These TPE derivative self-assemblies are formed due to two main important properties: (i) the TPE-core along with alkyl chains, optimizing the dispersive interactions within a construct, and (ii) amide-linkage through molecular recognition. We believe such arrangements prevent crystallization and favour the directional growth of flower-shape nanostructures in a 3D fashion.
Highlights
Supramolecular self-assemblies of small aromatic organic π-conjugated molecules have attracted enormous attention of researchers due to their applicability in optoelectronics, chemosensors, nanotechnology, biotechnology and biomedicines[1,2,3,4,5,6]
As part of our on-going program, we investigated the synthesis of dumbbell-shape TPE-1 and TPE-2 amphiphilic molecules (Fig. 1)
Both TPE-1 and TPE-2 compounds were synthesized by amide coupling of amino-TPE and alkyl-dicarboxylic acid and alkyl-carboxylic acid in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) and 4-dimethylaminopyridine (DMAP) in dry DMF, the synthetic procedure shown in Scheme 1
Summary
Supramolecular self-assemblies of small aromatic organic π-conjugated molecules have attracted enormous attention of researchers due to their applicability in optoelectronics, chemosensors, nanotechnology, biotechnology and biomedicines[1,2,3,4,5,6]. The organic flower-shaped morphology field is in its infancy and has not been explored with respect to AIE-active small organic molecules To further explore this idea, tetraphenylethylene (TPE) was used due to its aggregation induced emission (AIE) properties[28], contrary to the ACQ-effect[27] of most commonly used small molecules in flower assembly. It is a non-planar, propeller shaped molecule, which is prepared with excellent yield. TPE is widely used in various fields, designing small organic molecules with the potential of producing well-organised supramolecular nanostructures with efficient luminescence in solid states is still rare
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