Tuning of Thermochromic Properties of Polydiacetylene toward Universal Temperature Sensing Materials through Amido Hydrogen Bonding

Abstract

Mono-and diamides derivatives of 10,12-pentacosadiynoic acid (PCDA) were synthesized from condensation of PCDA with various aliphatic and aromatic diamines. Polydiacetylenes of the amido-PCDA derivatives were prepared by photopolymerization of their molecular assembly homogeneously dispersed in aqueous media. Thermochromic properties of the resulting polydiacetylene sol were studied by temperature variable UV-vis spectrometry along with photographic recording. The color transition temperatures and thermochromic reversibility of the polymers are varied depended on the number of amide groups and the structure of the aliphatic and aromatic linkers. The phenylenediamide and polymethylenediamide PCDA derivatives give polydiacetylenes with complete thermochromic reversibility, while the polydiacetylenes obtained from 1,2-cyclohexylene and glycolic chain diamide derivatives exhibited irreversible thermochromism, whereas the polymers attained from the aromatic monoamide analogues are partially reversible. The variation of the linkers also allows the color transition temperature of the polydiacetylene to be tuned in the range of 20 °C to over 90 °C. The results provide a fundamental idea about the factors affecting the thermochromic properties of polydiacetylenes toward the development of materials for universal thermal indicators.

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.…”

“…The thermochromism of PDA vesicles with carboxylic head groups is normally an irreversible process. One can tune the color-transition temperature of PDA vesicles by controlling the strength of interactions between side chains [1,5,21,22,27]. This is accomplished by varying length of side chains and type of the polar head groups.…”

“…This is accomplished by varying length of side chains and type of the polar head groups. When the interactions of side chains are strong enough, the color transition can occurs in a reversible fashion [1,21,25,27,28,34]. Comprehensive studies by Kim's group demonstrate that the increase of hydrogen bonding and p-p interaction at the surface of PDA vesicles results in a reversible thermochromism [1,27].…”

Thermoluminescent microparticle thermal history sensors

“…The group of Huang 16 has used TiO 2 nanoparticles as sensors by analyzing changes in their Raman spectra after they have grown during heating. Researchers such as Mecerreyes 17 and Sukwattanasinitt 18 have developed irreversible thermochromic materials to record and visually indicate temperature maximums through altered spectral absorbance. Most of the remaining few thermal history sensors utilize fluorescence and photoluminescence in some form.…”

Dye Sublimation as a Measure of Accumulated Heat Exposure

“…[3,4] Many diacetylene derivatives have been synthesized and tested as functional materials of the TTIs. [5] This type of TTI has been adopted by World Health Organization (WHO) as vaccine vial monitors. [6] However, this approach still has several disadvantages.…”