Tuning Down of Color Transition Temperature of Thermochromically Reversible Bisdiynamide Polydiacetylenes

Abstract

A series of bisdiynamide lipids containing various lengths of methylene spacer (m = 2, 3 and 4) between the diynes and the diamide headgroup and number of methylene units (n = 6 and 9) in their hydrophobic tails are synthesized. All six lipids synthesized can be dispersed in water and photopolymerized by UV irradiation to give the corresponding polydiacetylene (PDA) sols. The color transitions from blue to red during heating-cooling cycles of the PDA sols are photographically recorded and monitored by UV-vis absorption spectroscopy. The bisdiynamide PDAs exhibit excellent thermochromic reversibility and the color transition temperature can be tuned between ca. 25-55 °C by the variation of m and n values. Temperature indicators can be obtained by applying a screen printing ink formulated from the bisdiynamide monomer on plastic substrates followed by UV irradiation to generate desired patterns of thermochromically reversible PDAs.

Roles of head group architecture and side chain length on colorimetric response of polydiacetylene vesicles to temperature, ethanol and pH

“…Many research groups have demonstrated that structural modification of head group and side chain is a very effective approach for tuning the colorimetric response of PDA assemblies [13][14][15]33,[44][45][46][47]. Comprehensive studies by Kim and coworkers have shown that the strength of interactions at PDA vesicle surface strongly dictates the color-transition temperature [13,14].…”

“…In the extreme cases where the interactions between head groups are very strong, the color transition of PDA assemblies, usually an irreversible process, changes to the reversible one. The structural modification by bonding the head groups together also yields PDA assemblies with reversible thermochromism [15,[45][46][47]. However, most of these works mainly focuses on the colorimetric response to temperature.…”

A thermally reversible supramolecular system based on biphenyl polydiacetylene

“…Although some PDA system displayed reversible thermochromism, but in most of the cases reported earlier, reversible thermochromism was observed only in the narrow temperature range, for example 25-55 8C [33], or they were not fully reversible as they deteriorate to violet to red rather than blue to red after first heating-cooling cycle [34]. In the investigation described below, we prepared a new polydiacetylene, (Bip-PDA), in which biphenylcarboxylic acid group is connected in its side chain, the biphenyl group provides strong aromatic interaction between monomers and carboxylic acid induces intermolecular H-bonding during self-assembly.…”

Role of Gel to Fluid Transition Temperatures of Polydiacetylene Vesicles with 10,12-Pentacosadiynoic Acid and Cholesterol in Their Thermochromisms

“…[2][3][4][5][6][7][8][9][10][11][12][13][14] In the latter case, the applications rely on their ability to change colors in response to temperature, 15 pH, 16 receptors, [17][18][19][20][21] and other molecules 22 in a system. In addition, the flexibility of the precursors of polydiacetylenes to construct a variety of micro-or nanostructures (depending on the preparation methods) makes it possible to use them for the desired purposes.…”