Switchable structural modification accompanying altered optical properties of a zwitterionic polysquaraine

Lu, Hsiao‐Chi; Whang, Wha–Tzong; Cheng, Bing‐Ming

doi:10.1016/j.cplett.2010.10.023

Cited by 11 publications

(3 citation statements)

References 42 publications

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“…The synthesis of PMPS was first reported in 1965 [2] as one of the first squaraine compounds, which also included mention of poly(1H-pyrrol-2-ylsquaraine). Poly(1H-pyrrol-2-ylsquaraines) has been independently studied since 1965 but not for particle morphology, [3][4][5][6][7][8][9][10][11] except for a recent report that has done just that with respect to sodium ion storage as it applies to sodium-ion batteries. [12] The original synthesis of PMPS in the Triebs and Jacob paper [2] implied reflux of the two constituent reactants in ethanol, from which the precipitate was separated as a blue to blue-green insoluble polymer.…”

Section: Introductionmentioning

confidence: 99%

An investigation into the preparation of poly(1‐methylpyrol‐2‐ylsquaraine) particles

Lynch

2020

Journal of Heterocyclic Chem

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Poly(1‐methylpyrol‐2‐ylsquaraine) particles can be prepared in a one‐pot reaction by refluxing equimolar amounts of squaric acid (3,4‐dihydroxycyclobut‐3‐ene‐1,2‐dione) and 1‐methylpyrrole in butan‐1‐ol and precipitate from the reaction as porous micrometer‐sized spheres that have potential use as molecular adsorbents in chromatography and sensors, as well as ion batteries. Previous papers that have examined the electrical, photophysical, and adsorption properties of these particles have reported their size and shape, with appropriate proof in the form of electron microscope images but have paid little attention as to the actual limits of the particle size and spherical formation. Thus, a range of experiments have been undertaken to examine the robustness, in terms of reaction variation, of the construction of these spheres. Reaction characteristics such as solvent, sequence in which reactants are added, reaction time, reactant concentration, and mode of reaction agitation have all been examined to determine the optimal conditions for the production of these spheres. Fortuitously, butan‐1‐ol remains the most suitable solvent, but reactant concentration is important to produce uniformly sized spherical particles with minimal interparticle growth.

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Section: Introductionmentioning

confidence: 99%

An investigation into the preparation of poly(1‐methylpyrol‐2‐ylsquaraine) particles

Lynch

2020

Journal of Heterocyclic Chem

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“…The reason why this is important, particularly in this case, is because PMPS particles are very porous and can be collected, washed and dried while still containing significant amounts of reaction byproduct [92]. In terms of the micromolecular structure of pyrrole-derived polysquaraines, studies on type I polysquaraines have reported a switchable structure induced by both metal ions [42] and metal surfaces [47,65].…”

Section: Molecular Structurementioning

confidence: 99%

Pyrrolyl Squaraines–Fifty Golden Years

Lynch

2015

Metals

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Pyrrolyl squaraines, both dyes and polymers, were first reported in 1965 and since then a fascinating body of work has been produced investigating the chemistry of these interesting molecules. A major aspect of these molecules that makes them so appealing to those researchers who have contributed to this field over the last 50 years is their chemical versatility. In this review, subjects, such as the synthetic history, an understanding of the molecular structure, an overview of the optical properties, a discussion of both the electrical conduction properties, and magnetic properties, plus use of the particles of pyrrolyl squaraines, are presented. Furthermore, previously published results are not just presented; they are in certain cases collated and used to both highlight and explain important aspects of pyrrolyl squaraine chemistry.

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“…In each of these, pyrrole molecules both a-positions are free, promoting ease of polymerization. Mention of the polysquaraine made from 1H-pyrrole (or its derivatives substituted in the 3-or 4-position) in the literature (Binda et al, 2009;Chenthamarakshan and Ajayaghosh, 1998a;Chenthamarakshan et al, 1999a;Hasegawa et al, 2009;Ko et al, 2011;Lu et al, 2010aLu et al, ,b, 2013Jacob, 1965, 1966) is about equal (in terms of numbers of articles) to mention of the polysquaraine made from 1-methylpyrrole (Begum et al, 2010;Courgneau et al, 2013;Lynch et al, 2001Lynch et al, , 2005Lynch, 2011;Sant'Ana et al, 2006;Spicer et al, 2006;Jacob, 1965, 1966;Yu et al, 1990), with both limited by the fact that (without the aid of 3-position substituted long alkyl chains on the pyrrole groups to aid solubility) they can best be described as 'black intractable powders'. Irrespective of this, poly(1-methylpyrrol-2-ylsquaraine) (PMPS) particles have been studied for third-order nonlinear optical properties (Yu et al, 1990), both electrical conduction (Sant'Ana et al, 2006) and electrical insulation properties (Lynch et al, 2001); utilized for their size and shape to produce hollow silica particles (Lynch et al, 2005) and core-shell particles (Begum et al, 2010), used as support particles for the addition of ammonium phosphate in polymer fibres (Spicer et al, 2006), and used as an odour adsorbent agent (Courgneau et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

The uptake of metal elements into poly(1-methylpyrrol-2-ylsquaraine) particles and a study of their porosity

Lynch¹,

Bennett

Bateman

et al. 2016

Adsorption Science & Technology

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The article reports an experimental study of the metal uptake properties of poly(1-methylpyrrol-2-ylsquaraine) particles, in the context of 51 elemental metal complexes. Vagaries of the experimental results meant that the final analysis took place for 43 of these metals. After an initial descriptive analysis, an Analysis of Variance model was fitted. This revealed that several factors, some intrinsic to the metals themselves, others relating to the experimental conditions, have an important influence on the adsorption characteristics of the poly(1-methylpyrrol-2-ylsquaraine) particles. Of these, the most important is the ratio of the number of moles of the metal to the number of moles of the adsorbent particles. X-ray mapping of the poly(1-methylpyrrol-2-ylsquaraine) particles treated with contrast agent revealed that, although adsorption was all throughout the particles, the majority of the agent was adsorbed within 10-15% (diameter distance) of the surface of the particles.

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Switchable structural modification accompanying altered optical properties of a zwitterionic polysquaraine

Cited by 11 publications

References 42 publications

An investigation into the preparation of poly(1‐methylpyrol‐2‐ylsquaraine) particles

An investigation into the preparation of poly(1‐methylpyrol‐2‐ylsquaraine) particles

Pyrrolyl Squaraines–Fifty Golden Years

The uptake of metal elements into poly(1-methylpyrrol-2-ylsquaraine) particles and a study of their porosity

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