Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues

The effect of the phenyl–alkyl connecting group on mesogenic properties of several series of isostructural compounds containing p-carborane (A and B), bicyclo[2.2.2]octane (C), and benzene (D) was investigated using thermal and optical methods. Results demonstrated that mesophase stability in the se...

Descripción completa

Detalles Bibliográficos
Autores principales: Jankowiak, Aleksandra, Kaszynski, Piotr, Tilford, William R, Ohta, Kiminori, Januszko, Adam, Nagamine, Takashi, Endo, Yasuyuki
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2009
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2839553/
https://www.ncbi.nlm.nih.gov/pubmed/20300457
http://dx.doi.org/10.3762/bjoc.5.83
_version_ 1782178960794189824
author Jankowiak, Aleksandra
Kaszynski, Piotr
Tilford, William R
Ohta, Kiminori
Januszko, Adam
Nagamine, Takashi
Endo, Yasuyuki
author_facet Jankowiak, Aleksandra
Kaszynski, Piotr
Tilford, William R
Ohta, Kiminori
Januszko, Adam
Nagamine, Takashi
Endo, Yasuyuki
author_sort Jankowiak, Aleksandra
collection PubMed
description The effect of the phenyl–alkyl connecting group on mesogenic properties of several series of isostructural compounds containing p-carborane (A and B), bicyclo[2.2.2]octane (C), and benzene (D) was investigated using thermal and optical methods. Results demonstrated that mesophase stability in the series containing A–D follows the order (Alk)CH(2)CH(2)– < (Alk)OOC– < (Alk)CH(2)O– < (Alk)COO–. Surprisingly, the connecting groups (Alk)CH(2)CH(2)– and (Alk)OOC– destabilize the mesophase significantly stronger for carboranes (A and B) than for carbocyclic derivatives (C and D). Analysis indicates that this effect may have quadrupolar and conformational origin.
format Text
id pubmed-2839553
institution National Center for Biotechnology Information
language English
publishDate 2009
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-28395532010-03-17 Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues Jankowiak, Aleksandra Kaszynski, Piotr Tilford, William R Ohta, Kiminori Januszko, Adam Nagamine, Takashi Endo, Yasuyuki Beilstein J Org Chem Full Research Paper The effect of the phenyl–alkyl connecting group on mesogenic properties of several series of isostructural compounds containing p-carborane (A and B), bicyclo[2.2.2]octane (C), and benzene (D) was investigated using thermal and optical methods. Results demonstrated that mesophase stability in the series containing A–D follows the order (Alk)CH(2)CH(2)– < (Alk)OOC– < (Alk)CH(2)O– < (Alk)COO–. Surprisingly, the connecting groups (Alk)CH(2)CH(2)– and (Alk)OOC– destabilize the mesophase significantly stronger for carboranes (A and B) than for carbocyclic derivatives (C and D). Analysis indicates that this effect may have quadrupolar and conformational origin. Beilstein-Institut 2009-12-30 /pmc/articles/PMC2839553/ /pubmed/20300457 http://dx.doi.org/10.3762/bjoc.5.83 Text en Copyright © 2009, Jankowiak et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Jankowiak, Aleksandra
Kaszynski, Piotr
Tilford, William R
Ohta, Kiminori
Januszko, Adam
Nagamine, Takashi
Endo, Yasuyuki
Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues
title Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues
title_full Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues
title_fullStr Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues
title_full_unstemmed Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues
title_short Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues
title_sort ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2839553/
https://www.ncbi.nlm.nih.gov/pubmed/20300457
http://dx.doi.org/10.3762/bjoc.5.83
work_keys_str_mv AT jankowiakaleksandra ringalkylconnectinggroupeffectonmesogenicpropertiesofpcarboranederivativesandtheirhydrocarbonanalogues
AT kaszynskipiotr ringalkylconnectinggroupeffectonmesogenicpropertiesofpcarboranederivativesandtheirhydrocarbonanalogues
AT tilfordwilliamr ringalkylconnectinggroupeffectonmesogenicpropertiesofpcarboranederivativesandtheirhydrocarbonanalogues
AT ohtakiminori ringalkylconnectinggroupeffectonmesogenicpropertiesofpcarboranederivativesandtheirhydrocarbonanalogues
AT januszkoadam ringalkylconnectinggroupeffectonmesogenicpropertiesofpcarboranederivativesandtheirhydrocarbonanalogues
AT nagaminetakashi ringalkylconnectinggroupeffectonmesogenicpropertiesofpcarboranederivativesandtheirhydrocarbonanalogues
AT endoyasuyuki ringalkylconnectinggroupeffectonmesogenicpropertiesofpcarboranederivativesandtheirhydrocarbonanalogues

Ejemplares similares