Chiral amplification of disodium cromoglycate chromonics induced by a codeine derivative

F. Berride; E. Troche-Pesqueira; G. Feio; E. J. Cabrita; T. Sierra; A. Navarro-Vázquez; M. M. Cid

doi:10.1039/C7SM01227F

Chiral amplification of disodium cromoglycate chromonics induced by a codeine derivative†

F. Berride,‡^a E. Troche-Pesqueira,

‡^a G. Feio,^b E. J. Cabrita,

^c T. Sierra,

^d A. Navarro-Vázquez

*^e and M. M. Cid

*^a

Author affiliations

* Corresponding authors

^a Departamento de Quıímica Orgánica, Edificio de Ciencias Experimentais, Campus Lagoas-Marcosende, Vigo, Spain
E-mail: mcid@uvigo.es
Fax: +34986812262
Tel: +34986813563

^b CENIMAT-I3N, Departamento de Ciência dos Materiais, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Caparica, Portugal

^c UCIBIO, REQUIMTE, Departamento de Química, Facultade de Ciências e Tecnologia, Universidade Nova de Lisboa, Portugal

^d Instituto de Ciencia de Materiales de Aragón, Facultad de Ciencias, Pza. San Francisco, s/n – 50009 Zaragoza, Spain

^e Departamento de Química Fundamental, Universidade Federal de Pernambuco, Cidade Universitária, Recife, Brazil

Abstract

Chromonic liquid crystals (CLC) are lyotropic phases formed by discotic mesogens in water. Simple chiral dopants such as amino acids have been reported to turn chromonic liquid crystals into their cholesteric counterparts. Here we report a chirality amplification effect in the nematic phase of a 9 wt% disodium cromoglycate (DSCG) lyotropic liquid crystal (LLC) upon doping with a water-soluble codeine derivative. The transition on cooling the isotropic to the nematic phase showed the presence of homochiral spindle-shaped droplets (tactoids). NMR DOSY experiments on a triple gradient probe revealed a small degree of diffusion anisotropy for the alkaloid embedded in the liquid crystal structure. These results in combination with XRD, CD and POM experiments agree with a supramolecular aggregation model based on simple columnar stacks.

Supplementary files

Article information

DOI: https://doi.org/10.1039/C7SM01227F
Article type: Paper
Submitted: 21 Jun 2017
Accepted: 07 Aug 2017
First published: 08 Aug 2017

Download Citation

Soft Matter, 2017,13, 6810-6815

Permissions

Request permissions

Chiral amplification of disodium cromoglycate chromonics induced by a codeine derivative

F. Berride, E. Troche-Pesqueira, G. Feio, E. J. Cabrita, T. Sierra, A. Navarro-Vázquez and M. M. Cid, Soft Matter, 2017, 13, 6810 DOI: 10.1039/C7SM01227F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Soft Matter

Chiral amplification of disodium cromoglycate chromonics induced by a codeine derivative†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Chiral amplification of disodium cromoglycate chromonics induced by a codeine derivative

Social activity

Search articles by author

Spotlight

Advertisements