New chiral discotics with helical organization of the mesophase : liquid crystalline derivatives of dibenzotetraaza[14]annulene

doi:10.1016/j.tet.2012.03.037

New chiral discotics with helical organization of the mesophase : liquid crystalline derivatives of dibenzotetraaza[14]annulene

Communities & Collections

pcg.skipToMenu

New chiral discotics with helical organization of the mesophase : liquid crystalline derivatives of dibenzotetraaza[14]annulene

View Usage Statistics

Bibliographic description

punktacja MEiN [2012 A]: 30

title:	New chiral discotics with helical organization of the mesophase : liquid crystalline derivatives of dibenzotetraaza[14]annulene
author:	Grolik Jarosław , Dudek Łukasz , Eilmes Julita , Eilmes Andrzej , Górecki Marcin, Frelek Jadwiga, Heinrich Benoît, Donnio Bertrand
journal title:	Tetrahedron
volume:	68
issue:	20
date of publication :	2012
pages:	3875-3884
ISSN:	0040-4020
eISSN:	1464-5416
DOI:	10.1016/j.tet.2012.03.037
language:	English
journal language:	English
abstract in English:	Two optically pure derivatives of dibenzotetraaza[14]annulene, bearing four (S)- or (R)- 3,7-dimethyloctoxy peripheral chiral tails, respectively, and two hydroxybenzoyl meso substituents were synthesized using a convergent multi-step route. The structure of the products was determined by $^{1}\textrm{H}$ and $^{13}\textrm{C}$ NMR spectroscopy, ESI-MS, and elemental analysis. The mesomorphic behavior of the two chiral compounds, deciphered by differential scanning calorimetry (DSC), small-angle X-ray diffractometry (SA-XRD), and polarizing optical microscopy (POM) investigations, revealed the induction of two lamello-columnar phases, i.e., columnar stacks con fi ned in smectic layers, whose columns may be ar- ranged either according to the pg rectangular planar symmetry (for the low-temperature phase) or without registry between vicinal layers (for the high-temperature mesophase). Evidence of a helical organization of the molecules in the mesophases was obtained using a combination of electronic circular dichroism (ECD) and SA-XRD results, Molecular Dynamics simulations and quantum-chemical calculations.
keywords in English:	dibenzotetraaza[14]annulene, SA-XRD, liquid crystals, supramolecular chirality, ECD spectroscopy, molecular Dynamics
departmental parameterization:	30
affiliation:	Wydział Chemii : Zakład Metod Obliczeniowych Chemii, Wydział Chemii : Zakład Chemii Organicznej
type:	journal article
subtype:	academic paper

Files in this item

Files	Size	Format	View
There are no files associated with this item.

This item appears in the following Collection(s)

Publikacje naukowe