Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases

Tetraphenylenes 2 with eight peripheral gallic esters were prepared in two steps from octamethoxytetraphenylene 1 in 19–72% yield. Investigation of the mesomorphic properties of 2 by DSC, POM and X-ray diffraction revealed that derivatives 2a–d with short alkoxy chain lengths (C(5)–C(8)) did not sho...

Descripción completa

Detalles Bibliográficos
Autores principales: Wuckert, Eugen, Hägele, Constanze, Giesselmann, Frank, Baro, Angelika, Laschat, Sabine
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2009
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2813710/
https://www.ncbi.nlm.nih.gov/pubmed/20126633
http://dx.doi.org/10.3762/bjoc.5.57
_version_ 1782176946449285120
author Wuckert, Eugen
Hägele, Constanze
Giesselmann, Frank
Baro, Angelika
Laschat, Sabine
author_facet Wuckert, Eugen
Hägele, Constanze
Giesselmann, Frank
Baro, Angelika
Laschat, Sabine
author_sort Wuckert, Eugen
collection PubMed
description Tetraphenylenes 2 with eight peripheral gallic esters were prepared in two steps from octamethoxytetraphenylene 1 in 19–72% yield. Investigation of the mesomorphic properties of 2 by DSC, POM and X-ray diffraction revealed that derivatives 2a–d with short alkoxy chain lengths (C(5)–C(8)) did not show any mesomorphic properties, whereas compounds 2e–i with C(9)–C(13) chains displayed rectangular columnar mesophases and compounds 2j–l with C(14)–C(16) chains displayed hexagonal columnar mesophases. Furthermore an anomalous odd-even effect of the clearing points of compounds 2e–l versus chain length was detected.
format Text
id pubmed-2813710
institution National Center for Biotechnology Information
language English
publishDate 2009
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-28137102010-02-01 Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases Wuckert, Eugen Hägele, Constanze Giesselmann, Frank Baro, Angelika Laschat, Sabine Beilstein J Org Chem Full Research Paper Tetraphenylenes 2 with eight peripheral gallic esters were prepared in two steps from octamethoxytetraphenylene 1 in 19–72% yield. Investigation of the mesomorphic properties of 2 by DSC, POM and X-ray diffraction revealed that derivatives 2a–d with short alkoxy chain lengths (C(5)–C(8)) did not show any mesomorphic properties, whereas compounds 2e–i with C(9)–C(13) chains displayed rectangular columnar mesophases and compounds 2j–l with C(14)–C(16) chains displayed hexagonal columnar mesophases. Furthermore an anomalous odd-even effect of the clearing points of compounds 2e–l versus chain length was detected. Beilstein-Institut 2009-10-21 /pmc/articles/PMC2813710/ /pubmed/20126633 http://dx.doi.org/10.3762/bjoc.5.57 Text en Copyright © 2009, Wuckert 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
Wuckert, Eugen
Hägele, Constanze
Giesselmann, Frank
Baro, Angelika
Laschat, Sabine
Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases
title Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases
title_full Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases
title_fullStr Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases
title_full_unstemmed Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases
title_short Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases
title_sort saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2813710/
https://www.ncbi.nlm.nih.gov/pubmed/20126633
http://dx.doi.org/10.3762/bjoc.5.57
work_keys_str_mv AT wuckerteugen saddleshapedtetraphenyleneswithperipheralgallicestersdisplayingcolumnarmesophases
AT hageleconstanze saddleshapedtetraphenyleneswithperipheralgallicestersdisplayingcolumnarmesophases
AT giesselmannfrank saddleshapedtetraphenyleneswithperipheralgallicestersdisplayingcolumnarmesophases
AT baroangelika saddleshapedtetraphenyleneswithperipheralgallicestersdisplayingcolumnarmesophases
AT laschatsabine saddleshapedtetraphenyleneswithperipheralgallicestersdisplayingcolumnarmesophases

Ejemplares similares