Chalcogen bonding and liquid crystallinity: Understanding the anomalous behaviour of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles (nSCB)

Ewan Cruickshank; Grant J. Strachan; John MD Storey; Corrie T. Imrie

doi:10.1016/j.molliq.2021.117094

Chalcogen bonding and liquid crystallinity: Understanding the anomalous behaviour of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles (nSCB)

Ewan Cruickshank, Grant J. Strachan, John MD Storey, Corrie T. Imrie^*

^*Corresponding author for this work

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

6 Citations (Scopus)

Abstract

The synthesis and characterisation of the first eleven members of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles series is reported. All eleven members show monotropic liquid crystal behaviour. The first six members are exclusively nematogenic, the seventh member shows nematic and smectic A phases, and the higher homologues only smectic A behaviour. A comparison of their transitional behaviour with that of the corresponding alkyl and alkyloxy-cyanobiphenyls reveals a new pattern of behaviour. Specifically, the nematic-isotropic transition temperatures show a large decrease on passing from the methylthio to ethylthio homologues. This unexpected behaviour is interpreted in terms of chalcogen bonding.

Original language	English
Article number	117094
Number of pages	7
Journal	Journal of molecular liquids
Volume	346
Early online date	28 Jul 2021
DOIs	https://doi.org/10.1016/j.molliq.2021.117094
Publication status	Published - Jan 2022

Keywords

4-(Alkylthio)[1,1-biphenyl]-4-carbonitriles
Alkylthio
Chalcogen bonding
Nematic phase
Smectic A phase

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title = "Chalcogen bonding and liquid crystallinity: Understanding the anomalous behaviour of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles (nSCB)",

abstract = "The synthesis and characterisation of the first eleven members of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles series is reported. All eleven members show monotropic liquid crystal behaviour. The first six members are exclusively nematogenic, the seventh member shows nematic and smectic A phases, and the higher homologues only smectic A behaviour. A comparison of their transitional behaviour with that of the corresponding alkyl and alkyloxy-cyanobiphenyls reveals a new pattern of behaviour. Specifically, the nematic-isotropic transition temperatures show a large decrease on passing from the methylthio to ethylthio homologues. This unexpected behaviour is interpreted in terms of chalcogen bonding.",

keywords = "4-(Alkylthio)[1,1-biphenyl]-4-carbonitriles, Alkylthio, Chalcogen bonding, Nematic phase, Smectic A phase",

author = "Ewan Cruickshank and Strachan, {Grant J.} and Storey, {John MD} and Imrie, {Corrie T.}",

note = "Acknowledgement This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors. ",

year = "2022",

month = jan,

doi = "10.1016/j.molliq.2021.117094",

language = "English",

volume = "346",

journal = "Journal of molecular liquids",

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T1 - Chalcogen bonding and liquid crystallinity

T2 - Understanding the anomalous behaviour of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles (nSCB)

AU - Cruickshank, Ewan

AU - Strachan, Grant J.

AU - Storey, John MD

AU - Imrie, Corrie T.

N1 - Acknowledgement This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

PY - 2022/1

Y1 - 2022/1

N2 - The synthesis and characterisation of the first eleven members of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles series is reported. All eleven members show monotropic liquid crystal behaviour. The first six members are exclusively nematogenic, the seventh member shows nematic and smectic A phases, and the higher homologues only smectic A behaviour. A comparison of their transitional behaviour with that of the corresponding alkyl and alkyloxy-cyanobiphenyls reveals a new pattern of behaviour. Specifically, the nematic-isotropic transition temperatures show a large decrease on passing from the methylthio to ethylthio homologues. This unexpected behaviour is interpreted in terms of chalcogen bonding.

AB - The synthesis and characterisation of the first eleven members of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles series is reported. All eleven members show monotropic liquid crystal behaviour. The first six members are exclusively nematogenic, the seventh member shows nematic and smectic A phases, and the higher homologues only smectic A behaviour. A comparison of their transitional behaviour with that of the corresponding alkyl and alkyloxy-cyanobiphenyls reveals a new pattern of behaviour. Specifically, the nematic-isotropic transition temperatures show a large decrease on passing from the methylthio to ethylthio homologues. This unexpected behaviour is interpreted in terms of chalcogen bonding.

KW - 4-(Alkylthio)[1,1-biphenyl]-4-carbonitriles

KW - Alkylthio

KW - Chalcogen bonding

KW - Nematic phase

KW - Smectic A phase

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U2 - 10.1016/j.molliq.2021.117094

DO - 10.1016/j.molliq.2021.117094

M3 - Article

AN - SCOPUS:85112609390

VL - 346

JO - Journal of molecular liquids

JF - Journal of molecular liquids

SN - 0167-7322

M1 - 117094

ER -

Chalcogen bonding and liquid crystallinity: Understanding the anomalous behaviour of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles (nSCB)

Abstract

Keywords

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