Journal of Physical Chemistry C

, volume 118 , issue 43 , pages 25176-25189

Symmetrically Disubstituted Bithiophene Derivatives of 1,3,4-Oxadiazole, 1,3,4-Thiadiazole, and 1,2,4-Triazole – Spectroscopic, Electrochemical, and Spectroelectrochemical Properties

Aleksandra Kurowska ¹

Anastasia S. Kostyuchenko ^{2, 3}

Pawel Zassowski ¹

Lukasz Skorka ⁴

Viacheslav L Yurpalov ²

Alexander S. Fisyuk ^{2, 3}

A. Pron ⁴

Wojciech Domagala ¹

Hide authors affiliations Show authors affiliations: 4 affiliations

Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland |

Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation |

Laboratory of New Organic Materials, Omsk State Technical University, Mira ave. 11, Omsk 644050, Russian Federation |

⁴

Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland |

Publication type: Journal Article

Publication date: 2014-10-17

American Chemical Society (ACS)

Journal of Physical Chemistry C

scimago Q1

wos Q3

SJR: 0.914

CiteScore: 6.2

Impact factor: 3.2

ISSN: 19327447, 19327455

DOI: 10.1021/jp507838c

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Surfaces, Coatings and Films

Electronic, Optical and Magnetic Materials

Physical and Theoretical Chemistry

General Energy

Abstract

Electrochemical and spectroelectrochemical properties of a series of new penta-ring donor–acceptor compounds, comprising 1,3,4-oxadiazole, 1,3,4-thiadiazole, and 1,2,4-triazole central ring, symmetrically connected to substituted bithiophenes, were investigated. Aromaticity and electrophilic–nucleophilic traits of the aza-heterocyclic units, fostering inductive and resonance effects that translate to conjugation enhancement and electron (de)localization, were found a major factor determining the key electron properties of ionization potential (IP) and electron affinity (EA) of these molecules. Replacing the alkyl thiophene substituent for an alkoxy one afforded certain control over the two parameters as well. All studied compounds were found to undergo electrochemical polymerization giving p- and n-dopable products, featuring good electrochemical reversibility of their oxidative doping process, as demonstrated by cyclic voltammetry and UV–vis–NIR, EPR spectroelectrochemistry. While electropolymerization o...

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Kurowska A. et al. Symmetrically Disubstituted Bithiophene Derivatives of 1,3,4-Oxadiazole, 1,3,4-Thiadiazole, and 1,2,4-Triazole – Spectroscopic, Electrochemical, and Spectroelectrochemical Properties // Journal of Physical Chemistry C. 2014. Vol. 118. No. 43. pp. 25176-25189.

GOST all authors (up to 50) Copy

Kurowska A., Kostyuchenko A. S., Zassowski P., Skorka L., Yurpalov V. L., Fisyuk A. S., Pron A., Domagala W. Symmetrically Disubstituted Bithiophene Derivatives of 1,3,4-Oxadiazole, 1,3,4-Thiadiazole, and 1,2,4-Triazole – Spectroscopic, Electrochemical, and Spectroelectrochemical Properties // Journal of Physical Chemistry C. 2014. Vol. 118. No. 43. pp. 25176-25189.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/jp507838c

UR - https://doi.org/10.1021/jp507838c

TI - Symmetrically Disubstituted Bithiophene Derivatives of 1,3,4-Oxadiazole, 1,3,4-Thiadiazole, and 1,2,4-Triazole – Spectroscopic, Electrochemical, and Spectroelectrochemical Properties

T2 - Journal of Physical Chemistry C

AU - Kurowska, Aleksandra

AU - Kostyuchenko, Anastasia S.

AU - Zassowski, Pawel

AU - Skorka, Lukasz

AU - Yurpalov, Viacheslav L

AU - Fisyuk, Alexander S.

AU - Pron, A.

AU - Domagala, Wojciech

PY - 2014

DA - 2014/10/17

PB - American Chemical Society (ACS)

SP - 25176-25189

IS - 43

VL - 118

SN - 1932-7447

SN - 1932-7455

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2014_Kurowska,

author = {Aleksandra Kurowska and Anastasia S. Kostyuchenko and Pawel Zassowski and Lukasz Skorka and Viacheslav L Yurpalov and Alexander S. Fisyuk and A. Pron and Wojciech Domagala},

title = {Symmetrically Disubstituted Bithiophene Derivatives of 1,3,4-Oxadiazole, 1,3,4-Thiadiazole, and 1,2,4-Triazole – Spectroscopic, Electrochemical, and Spectroelectrochemical Properties},

journal = {Journal of Physical Chemistry C},

year = {2014},

volume = {118},

publisher = {American Chemical Society (ACS)},

month = {oct},

url = {https://doi.org/10.1021/jp507838c},

number = {43},

pages = {25176--25189},

doi = {10.1021/jp507838c}

}

MLA

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Kurowska, Aleksandra, et al. “Symmetrically Disubstituted Bithiophene Derivatives of 1,3,4-Oxadiazole, 1,3,4-Thiadiazole, and 1,2,4-Triazole – Spectroscopic, Electrochemical, and Spectroelectrochemical Properties.” Journal of Physical Chemistry C, vol. 118, no. 43, Oct. 2014, pp. 25176-25189. https://doi.org/10.1021/jp507838c.