A density functional theory study of the structural preferences of Type B heteropentalene mesomeric betaines and their non-aromatic azacyclooctatetraene isomers

Jake Bell; Mark T. Sims; Stephen P. Stanforth

doi:10.1002/jhet.70174

A density functional theory study of the structural preferences of Type B heteropentalene mesomeric betaines and their non-aromatic azacyclooctatetraene isomers

Jake Bell, Mark T. Sims, Stephen P. Stanforth^*

^*Corresponding author for this work

School of Geography and Natural Sciences

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Abstract

Density Functional Theory (DFT) has been used to explore the relative thermodynamic stabilities of a series of Type B heteropentalene mesomeric betaines (HMBs) 1a-c and their corresponding azacyclooctatetraene isomers 2a-c. The results of these calculations suggest that (a) the interconversion of most pairs of isomers is unlikely to occur and (b) the HOMO/LUMO energy difference in the HMBs suggests they might have a role in reducing the band gaps of known Type B HMB conducting polymers.

Original language	English
Pages (from-to)	1-7
Number of pages	7
Journal	Journal of Heterocyclic Chemistry
Early online date	12 Feb 2026
DOIs	https://doi.org/10.1002/jhet.70174
Publication status	E-pub ahead of print - 12 Feb 2026

Keywords

azacyclooctatetraenes
DFT
heteropentalene mesomeric betaines
isomerization
thermodynamic stability

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10.1002/jhet.70174Licence: CC BY

J Het Chem 2026 paper final accepted version with supporting infoAccepted author manuscript, 958 KBLicence: CC BY
Journal of Heterocyclic Chem - 2026 - Bell - A Density Functional Theory Study of the Structural Preferences of Type BFinal published version, 560 KBLicence: CC BY

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title = "A density functional theory study of the structural preferences of Type B heteropentalene mesomeric betaines and their non-aromatic azacyclooctatetraene isomers",

abstract = "Density Functional Theory (DFT) has been used to explore the relative thermodynamic stabilities of a series of Type B heteropentalene mesomeric betaines (HMBs) 1a-c and their corresponding azacyclooctatetraene isomers 2a-c. The results of these calculations suggest that (a) the interconversion of most pairs of isomers is unlikely to occur and (b) the HOMO/LUMO energy difference in the HMBs suggests they might have a role in reducing the band gaps of known Type B HMB conducting polymers.",

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author = "Jake Bell and Sims, \{Mark T.\} and Stanforth, \{Stephen P.\}",

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doi = "10.1002/jhet.70174",

language = "English",

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T1 - A density functional theory study of the structural preferences of Type B heteropentalene mesomeric betaines and their non-aromatic azacyclooctatetraene isomers

AU - Bell, Jake

AU - Sims, Mark T.

AU - Stanforth, Stephen P.

PY - 2026/2/12

Y1 - 2026/2/12

N2 - Density Functional Theory (DFT) has been used to explore the relative thermodynamic stabilities of a series of Type B heteropentalene mesomeric betaines (HMBs) 1a-c and their corresponding azacyclooctatetraene isomers 2a-c. The results of these calculations suggest that (a) the interconversion of most pairs of isomers is unlikely to occur and (b) the HOMO/LUMO energy difference in the HMBs suggests they might have a role in reducing the band gaps of known Type B HMB conducting polymers.

AB - Density Functional Theory (DFT) has been used to explore the relative thermodynamic stabilities of a series of Type B heteropentalene mesomeric betaines (HMBs) 1a-c and their corresponding azacyclooctatetraene isomers 2a-c. The results of these calculations suggest that (a) the interconversion of most pairs of isomers is unlikely to occur and (b) the HOMO/LUMO energy difference in the HMBs suggests they might have a role in reducing the band gaps of known Type B HMB conducting polymers.

KW - azacyclooctatetraenes

KW - DFT

KW - heteropentalene mesomeric betaines

KW - isomerization

KW - thermodynamic stability

UR - https://www.scopus.com/pages/publications/105029823090

U2 - 10.1002/jhet.70174

DO - 10.1002/jhet.70174

M3 - Article

SN - 0022-152X

SP - 1

EP - 7

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

ER -

A density functional theory study of the structural preferences of Type B heteropentalene mesomeric betaines and their non-aromatic azacyclooctatetraene isomers

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Keywords

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