Aggregation‐Dependent Chromism and Photopolymerization of Aminoanthraquinone‐Substituted Diacetylenes

Abstract

Polydiacetylenes have attracted significant interest for their unique chromatic properties and applications in sensing, imaging, and optics. Here, it is demonstrated that aminoanthraquinone‐substituted diacetylenes exhibit distinct aggregation‐dependent chromatic properties, affected by the alignment of both the aminoanthraquinone headgroups and diacetylene sidechains. Specifically, it is shown that aminoanthraquinone‐diacetylene monomers adopt different film organizations depending upon the polarity of the solvent employed for predissolution. In particular, a yellow aminoanthraquinone‐diacetylene phase, which undergoes photopolymerization upon ultraviolet irradiation, is produced upon dissolution in polar organic solvents prior to deposition and drying on solid substrates. In contrast, a red phase that can not be polymerized is observed when the monomers are predissolved in apolar solvents. Microscopic and spectroscopic analyses indicate that the optical properties of the films are determined by the degree of overlap between the aminoanthraquinone headgroups as well as the alignment of the diacetylene sidechains; both factors are intimately affected by interactions of the monomers with solvent molecules. It is shown that the aggregation‐dependent diacetylene films exhibit remarkable solvochromic, thermochromic, and mechanochromic properties. The aminoanthraquinone‐substituted diacetylenes may facilitate chromatic tuning of polydiacetylene systems in the solid state, determined by solvent‐ and intermolecular interactions and concomitant self‐assembly of the pendant sidechains and aromatic headgroups.

A writable aniline‐functionalized polydiacetylene composite with obvious colorimetric change upon both heating and near infrared lights irradiation

“…PDAs displaying aromatic headgroups in the side chains possess some distinctive morphological, optical, and electronic properties. 22 In this work, aniline substituted diacetylene monomer (PCDA-AN) was synthesized according to the previous report by amidation reaction of the commercially available diacetylic acid precursor (Scheme S1 and Figure S1). 23 The chemical structures of PCDA-AN and NIR dyes (IR-813 and IR-1064) are shown in Scheme 1.…”

Ultra-low-temperature reversible thermochromism and contactless bacterial sensing by chalcone-functionalized polydiacetylene

“…17,18 Recently developed anthraquinone functionalized PDA assemblies manifested interesting vapor sensing and mechano-chromic properties. 19…”

“…17,18 Recently developed anthraquinone functionalized PDA assemblies manifested interesting vapor sensing and mechano-chromic properties. 19 Chalcones are an important class of organic p-conjugated molecules naturally present in various food products. 20…”

Layered macrocycles with flexibility and tunable dynamic properties for wide-range thermoresponsive color changes

“…39 A wide variety of DA monomers and their assembled structures have been studied for control of the stimuli responsivity toward sensing applications. [40][41][42][43][44][45][46][47][48][49][50][51] The macrocycles containing DA moieties have been synthesized to obtain the self-assembled tubular PDA exhibiting thermochromism and solvatochromism. [52][53][54][55] However, control of the stimuli responsivity and structural flexibility is not easily achieved only by the molecular design.…”