Effect of ethanol on the color transition of the polydiacetylene vesicle of 10,12‐pentacosadiynoic acid for butylamine detection

Shin, Min Jae; Shin, Jae Sup

doi:10.1002/app.47688

Cited by 13 publications

(8 citation statements)

References 46 publications

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“…For the DXXDGD-PDA series, the absorbance data demonstrate that the differential interaction of a peripheral XX domain with the solvent does not significantly perturb the DA assembly and the conformation of the resulting peptide. [37][38][39][40][41] This is also consistent with the smaller MPI difference between DTTDGD vs. DVVDGD than that of DDGDTT vs. DDGDVV, as well as when comparing the MPI difference between the FF-vs. YY-substitution of DDGDXX and DXXDGD peptides. The collective absorbance profiles of PDAs from DDGDXX-and DXXDGD-PDA monomers show that the torsional impact of peptides on PDA conformation is significantly different when the substitution domain is closer to the solvent or to the diacetylene group even if the two substitution domain positions being compared here are just separated by 1 amino acid position.…”

Section: Steric Effects and Hydrophobic Interactions Within Peptide S...supporting

confidence: 81%

Steric and Hydrophobic Control Over Sequence-Defined Peptide Templates to Modulate the Properties of Polydiacetylene Nanomaterials

Kuang

Yao

Lim

et al. 2022

Preprint

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Precision control over molecular structure-function correlations in adaptive conjugated polymers such as polydiacetylene (PDA) is rarely demonstrated in completely aqueous environments due to solvent incompatibility, yet critical for realizing their biomedical applications. For PDAs, the chromogenic transitions that are key to their stimuli-responsiveness depend on the conformation and electronic structure of the π-conjugated backbone, which can be influenced by the nature of flanking, solubilizing groups that guide the topochemical polymerization of PDAs. Here, we investigate the dependence of amphiphilic polydiacetylene properties based on the characteristic contributions of amino acids that comprise the peptide segments serving as a biomimetic template for diacetylene polymerization in water. While sequence engineering has long been used as an effective approach to tune the function of peptide- or protein-based materials, it remains elusive how the interplay between steric effects and hydrophobicity at the residue level can impact the assembly behavior and the bulk properties of the resulting materials from hierarchically ordered 1-D nanostructures. We leverage the strict geometric requirements needed to topochemically polymerize diacetylenes bearing hexameric peptide moieties to systematically probe the impact of molecular volume and polarity changes brought by dipeptide substitution domains to the assembly behavior, photophysics, electrical properties, and biocompatibility of peptide-PDA assemblies. From a series of peptide-diacetylene monomers with systematically varied sequence, we show that steric contributions predominate the resulting photophysical properties, but the trends in the formation of higher order assemblies comprising the film bioscaffolds are distinct from the trends in PDA electronic structure changes driven by the peptide templates due to the combined impact of sterics and hydrophobicity. This work demonstrates how sequence-tunable, biomimetic interactions can be used as a synthetic handle to rationally tune PDA properties across length scales.

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Section: Steric Effects and Hydrophobic Interactions Within Peptide S...supporting

confidence: 81%

Steric and Hydrophobic Control Over Sequence-Defined Peptide Templates to Modulate the Properties of Polydiacetylene Nanomaterials

Kuang

Yao

Lim

et al. 2022

Preprint

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“…However, when PCDA is modified with an ethylenediamine headgroup, the polydiacetylene is able to distinguish between 1-propanol and 2-propanol or between 1-propanol and ethanol, which provides an important structure-specific insight into the chemical sensing properties of polydiacetylene-based materials . The presence of ethanol in PCDA vesicles results in swelling and an increase in size with increasing ethanol concentrations . The swelling of the vesicle results in the hydrogen bonds between the PCDA head groups breaking and weakens the dispersion interactions between the polydiacetylene side chains .…”

Section: Optical and Electronic Properties Of Polydiacetylenesmentioning

confidence: 94%

Properties and Applications of Stimuli-Responsive Diacetylenes

Hall

Musa

Steed

2021

Crystal Growth & Design

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The topochemical reactivity of diacetylene monomers has long been established and involves the 1,4-addition polymerization reaction. This reaction is governed by well-defined parameters that allow the synthesis of diacetylene polymers. Polydiacetylenes are conjugated polymers that display unique colorimetric and fluorescent transitions when they are exposed to a range of stimuli, allowing them to be easily exploited in biosensors, chemosensors, and radiochromic dosimeters. In this review, we summarize recent work on polydiacetylene systems, focusing on examples involving 10,12-pentacosadiynoic acid (PCDA) that can be structured as polymerized vesicles, films, gels, and powders. Synthetic derivatives of PCDA are also reviewed, along with the effect of incorporating guest molecules to a diacetylene system and establishing the important relationship between reversible thermochromism and noncovalent interactions.

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“…9 Our research group has previously reported several studies on sensor systems using PDA. Newly synthesized PDA systems for detecting specific chemical compounds, [10][11][12] gas sensors using PDA systems, 13 PDA systems involving molecular imprinting systems, 14 solvent effects in PDA systems, 15,16 and application of the layer-by-layer system to PDA systems have been reported. 13 A controlled drug delivery system is aimed to release the correct dose of a drug in the desired area and during the required time.…”

Section: Introductionmentioning

confidence: 99%

Relationship of color change to permeation of target compound in polydiacetylene vesicle system

Shin

2021

J of Applied Polymer Sci

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Polydiacetylene (PDA) systems, which showed color changes due to the permeation of target molecules, were reported previously by our research group. To use the systems for controlled drug delivery systems, the relationship of the color change to the permeation time of the PDA vesicle must be characterized precisely. Therefore, this relationship was investigated and characterized in this study. Methotrexate (MTX) was used as the target compound and the detection of MTX is an important process in anticancer study. N-(2-aminoethyl)pentacosa-10,12-diynamide (AEPCDA) was used as the diacetylene surfactant. Dimethyldioctadecylammonium bromide (DOAB) was used as an assistant surfactant. The color change occurred when the mixed surfactant vesicles, with DOAB, were used. When a lower ratio of DOAB was added to the AEPCDA vesicle, the color change rate was slower than that when using the higher ratio of DOAB. The color change rate constants were estimated for several different ratios (AEPCDA:DOAB). Surfactants with different carbon numbers to DOAB were used as the assistant surfactants in this study. The results showed that the color change rate constant decreased with the increasing carbon number of the assistant surfactant. This means that the color change rate can be controlled by changing the assistant surfactant.

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Effect of ethanol on the color transition of the polydiacetylene vesicle of 10,12‐pentacosadiynoic acid for butylamine detection

Cited by 13 publications

References 46 publications

Steric and Hydrophobic Control Over Sequence-Defined Peptide Templates to Modulate the Properties of Polydiacetylene Nanomaterials

Steric and Hydrophobic Control Over Sequence-Defined Peptide Templates to Modulate the Properties of Polydiacetylene Nanomaterials

Properties and Applications of Stimuli-Responsive Diacetylenes

Relationship of color change to permeation of target compound in polydiacetylene vesicle system

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