Aggregation-Induced Reversible Thermochromism of Novel Azo Chromophore-Functionalized Polydiacetylene Cylindrical Micelles

Abstract

We demonstrate a new strategy for improved stabilization of polydiacetylene micelles. They show temperature-induced color changes, which are fully reversible even at varying pH. A novel azo chromophore-functionalized amphiphilic diacetylene molecule is synthesized and used to prepare self-assembled cylindrical micelles. The micelles can be polymerized by 254 nm light irradiation. The azo chromophores form H- and J-like aggregates in the polydiacetylene micelles and increase the stability of the micelles, which leads to fully reversible thermochromism of the micelles in the temperature range between 20 and 90 °C and the pH range between 5.6 and 9.6.

Photon energy storage materials with high energy densities based on diacetylene–azobenzene derivatives

“…They can also be rapidly photopolymerized by UV illumination to produce polydiacetylenes bearing azobenzene-containing side chains on the rigid conjugated backbones, which resemble the structure of rigid templates decorated with closely-packed photochromic units. Previous efforts on azobenzene-decorated diacetylenes and polydiacetylenes have focused on asymmetric structures where azobenzene groups functionalized on one side and long alkyl chains on the other side are designed to enable the selfassembly of molecules into vesicles and tubes 25 or bilayer lms 26,27 for applications such as photocontrolled molecular recognition and reversible optical switch. 28 Building upon the knowledge gained in these studies regarding the structural change of the azobenzene-functionalized diacetylenes, we are able to design symmetric diacetylenes that enable the high loading and ordered arrangement of azobenzene groups.…”

Stable polydiacetylene/ZnO nanocomposites with two-steps reversible and irreversible thermochromism: The influence of strong surface anchoring

“…To realize its full potential, large amount of works have been carried out, seeking for method to manipulate the color-transition property of PDA. One of the very efficient approaches is the chemical modification of PDA side chains, which in turn affects the strength of intra-and interchain interactions [16,[20][21][22][23][24][25][26][27][28][29]. However, this method inevitably involves complicate synthetic procedures and requires expensive chemicals and/or catalysts.…”

Structure and Behavior of Polydiacetylene‐Based Micelles

“…The conjugate's ene-yne motif is prone to undergoing further conformational changes in response to external stimuli, such as temperature, pH, mechanical stress or solvent, [7,8] which leads to distinctive chromic transformations. As it happens, the color of the nanostructured polydiacetylenes changes from blue to red, leading to their application as colorimetric chemosensors or biomolecular sensors.…”