Synthesis and photophysical properties of 3,5-diaryl-2-heteroarylthiophenes

Ieva Karpavičienė; Mantas Jonušis; Kaspars Leduskrasts; Indrė Misiūnaitė; Edgars Suna; Inga Čikotienė

doi:10.1016/j.dyepig.2019.107646

Synthesis and photophysical properties of 3,5-diaryl-2-heteroarylthiophenes

Ieva Karpavičienė
, Mantas Jonušis
, Kaspars Leduskrasts
, Indrė Misiūnaitė
, Edgars Suna
, Inga Čikotienė^*

^*Corresponding author for this work

Vilnius University
Latvian Institute of Organic Synthesis

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

A series of 3,5-diaryl-2-heteroarylthiophenes have been synthesized via Fiesselmann type reaction between alkynones and easily available heteroarylmethanethiols or heteroarylmethyl carbamimidothioates. A correlation between compounds structure and efficiency of luminescence has been established. These compounds exhibited photoluminescence with quantum yields up to 83%. An evidence of twisted intramolecular charge transfer and singlet emissive states have been demonstrated.

Original language	English
Article number	107646
Journal	Dyes and Pigments
Volume	170
DOIs	https://doi.org/10.1016/j.dyepig.2019.107646
Publication status	Published - Nov 2019
Externally published	Yes

OECD Field of Science

1.3 Physical Sciences

Keywords

Fiesselmann reaction
Photoluminescence quantum yields
Solvatochromism
Trisubstituted monomeric thiophene
Twisted intramolecular charge transfer

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10.1016/j.dyepig.2019.107646

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@article{f5064d7bfd6c4e80bcd1de8fa4ec7648,

title = "Synthesis and photophysical properties of 3,5-diaryl-2-heteroarylthiophenes",

abstract = "A series of 3,5-diaryl-2-heteroarylthiophenes have been synthesized via Fiesselmann type reaction between alkynones and easily available heteroarylmethanethiols or heteroarylmethyl carbamimidothioates. A correlation between compounds structure and efficiency of luminescence has been established. These compounds exhibited photoluminescence with quantum yields up to 83\%. An evidence of twisted intramolecular charge transfer and singlet emissive states have been demonstrated.",

keywords = "Fiesselmann reaction, Photoluminescence quantum yields, Solvatochromism, Trisubstituted monomeric thiophene, Twisted intramolecular charge transfer",

author = "Ieva Karpavi{\v c}ienė and Mantas Jonu{\v s}is and Kaspars Leduskrasts and Indrė Misiūnaitė and Edgars Suna and Inga {\v C}ikotienė",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = nov,

doi = "10.1016/j.dyepig.2019.107646",

language = "English",

volume = "170",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Synthesis and photophysical properties of 3,5-diaryl-2-heteroarylthiophenes

AU - Karpavičienė, Ieva

AU - Jonušis, Mantas

AU - Leduskrasts, Kaspars

AU - Misiūnaitė, Indrė

AU - Suna, Edgars

AU - Čikotienė, Inga

PY - 2019/11

Y1 - 2019/11

N2 - A series of 3,5-diaryl-2-heteroarylthiophenes have been synthesized via Fiesselmann type reaction between alkynones and easily available heteroarylmethanethiols or heteroarylmethyl carbamimidothioates. A correlation between compounds structure and efficiency of luminescence has been established. These compounds exhibited photoluminescence with quantum yields up to 83%. An evidence of twisted intramolecular charge transfer and singlet emissive states have been demonstrated.

AB - A series of 3,5-diaryl-2-heteroarylthiophenes have been synthesized via Fiesselmann type reaction between alkynones and easily available heteroarylmethanethiols or heteroarylmethyl carbamimidothioates. A correlation between compounds structure and efficiency of luminescence has been established. These compounds exhibited photoluminescence with quantum yields up to 83%. An evidence of twisted intramolecular charge transfer and singlet emissive states have been demonstrated.

KW - Fiesselmann reaction

KW - Photoluminescence quantum yields

KW - Solvatochromism

KW - Trisubstituted monomeric thiophene

KW - Twisted intramolecular charge transfer

UR - https://www.sciencedirect.com/science/article/abs/pii/S0143720819307053 Nav precizēts

UR - https://www.scopus.com/pages/publications/85067657674

U2 - 10.1016/j.dyepig.2019.107646

DO - 10.1016/j.dyepig.2019.107646

M3 - Article

AN - SCOPUS:85067657674

SN - 0143-7208

VL - 170

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 107646

ER -

Synthesis and photophysical properties of 3,5-diaryl-2-heteroarylthiophenes

Abstract

OECD Field of Science

Keywords

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