Designing conducting polymer-based sensors: selective ionochromic response in crown ether-containing polythiophenes

Marsella, Michael J.; Swager, Timothy M.

doi:10.1021/ja00078a090

Cited by 305 publications

(203 citation statements)

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“…Although the excitation energies were slightly overestimated, the highest occupied molecular orbital-lowest unoccupied molecular orbital gap increased as the strap length increased, a tendency that agrees well with the experimental results (Supplementary Figure S5). 33 A previous study by our group, conceptually related to the present study, has demonstrated that the dihedral angle of bithiophene is affected by cyclic side chains. [34][35][36][37] In STBm/n (Scheme 2), the movable range of the dihedral angle of the bithiophene backbone was defined by the length of the strap.…”

Section: Synthesis Of Monomerssupporting

confidence: 51%

Twisting poly(3-substituted thiophene)s: cyclopolymerization of gemini thiophene monomers through catalyst-transfer polycondensation

Zhao

Nagura

Takeuchi

et al. 2016

Polym J

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Polythiophenes are an important class of materials in the field of organic electronics. The molecular structures of polythiophenes have a critical role in determining device performance; therefore, substantial efforts have been devoted to controlling their regioregularity, molecular weight and polydispersity. Herein, we demonstrate a new approach for controlling another structural parameter, the dihedral angle. We exploited the unique polymerization mechanism of cyclopolymerization: an alternating intramolecular-intermolecular chain propagation that produces a series of cyclic molecules along the polythiophene chain. We designed gemini thiophene monomers in which two thiophene monomers are tethered by an alkylene strap and we processed the monomers by using the catalyst-transfer polycondensation method. We found that the dihedral angle in the polythiophene is dictated by the size of the macrocycle formed.

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Section: Synthesis Of Monomerssupporting

confidence: 51%

Twisting poly(3-substituted thiophene)s: cyclopolymerization of gemini thiophene monomers through catalyst-transfer polycondensation

Zhao

Nagura

Takeuchi

et al. 2016

Polym J

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“…making EPs useful as sensors of gases, [6][7][8] metallic ions, [9][10][11][12] biomolecules, [14][15][16][17][18][19] etc, for environmental and clinical monitoring.…”

Section: Introductionmentioning

confidence: 99%

Fmoc–RGDS based fibrils: atomistic details of their hierarchical assembly

Zanuy

Poater

Solà

et al. 2016

Phys. Chem. Chem. Phys.

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The interaction between morphine (MO), a very potent analgesic psychoactive drug, and five electroactive polymers, poly(3,4-ethylenedioxythiophene) (PEDOT), poly(3-methylthiophene) (P3MT), polypyrrole (PPy), poly(N-methylpyrrole (PNMPy) and poly[N-(2-cyanoethyl)pyrrole] (PNCPy), has been examined using theoretical calculations on model complexes and voltammetric measures considering different pHs and incubation times. Quantum mechanical calculations in model polymers predict that the strength of the binding between the difference polymers and morphine increases as follows: PEDOT < PNMPy < PPy << P3MT ≈ PNCPy. The most relevant characteristic of P3MT is its ability to interact with morphine exclusively through non-directional interactions. On the other hand, the variations of the electroactivity and the anodic current at the reversal potential evidence that the voltammetric response towards the presence of MO is considerably higher for P3MT and PNCPy than that for the other polymers at both acid (P3MT > PNMPy) and neutral (P3MT ≈ PNCPy) pHs. Energy decomposition analyses of the interaction of MO with different model polymers indicate that the stronger affinity of MO for P3MT and PNCPy as compared to PEDOT, PNMPy, and PPy is due to more favorable orbital interactions. These more stabilizing orbital interactions are the result of the larger charge transfer from MO to P3MT and PNCPy model polymers that takes place because of the higher stability of the single occupied molecular orbital (SOMO) of these model polymers. Therefore, to design polymers with a large capacity to detect MO we suggest looking at polymers with high electron affinity.3

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“…3, was to produce a polythiophene that has the -bridged oligoethylene glycol which can bind alkali metal ions similar to a crown ether. 16 This molecular recognition produced large spectroscopic changes and with metal complexation, poly-1 underwent a large absorption blueshift (Á max ¼ À91 nm), consistent with the bithiophene axis twisting upon complexation with alkali metal ions. Twisting reduces -orbital overlap and the effective conjugation length.…”

Section: Conducting-polymer-based Chemical Sensorsmentioning

confidence: 88%

Conducting-Polymer-Based Chemical Sensors: Transduction Mechanisms

Sugiyasu¹,

Swager²

2007

Bulletin of the Chemical Society of Japan

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Conducting organic polymers show great promise as sensory materials. The transport of charge in these systems imparts the ability to attain high sensitivity to analytes of interest. This contribution reviews a number of different mechanisms by which analytes can interact with organic conducting polymers to create changes in their resistivity. New sensor systems based upon triaryl-methyl carbocations are also reported for the first time. The design of specific molecular recognition can impart selectivity in this process and in addition the nature of the conducting polymer can also lead to selectivity for different analytes.

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Designing conducting polymer-based sensors: selective ionochromic response in crown ether-containing polythiophenes

Cited by 305 publications

References 0 publications

Twisting poly(3-substituted thiophene)s: cyclopolymerization of gemini thiophene monomers through catalyst-transfer polycondensation

Twisting poly(3-substituted thiophene)s: cyclopolymerization of gemini thiophene monomers through catalyst-transfer polycondensation

Fmoc–RGDS based fibrils: atomistic details of their hierarchical assembly

Conducting-Polymer-Based Chemical Sensors: Transduction Mechanisms

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