Chiroptical properties of carbo[6]helicene derivatives bearing extended π-conjugated cyano substituents

Mehdi El Sayed Moussa; Monika Srebro; Emmanuel Anger; Nicolas Vanthuyne; Christian Roussel; Christophe Lescop; Jochen Autschbach; Jeanne Crassous

doi:10.1002/chir.22201

Chiroptical properties of carbo[6]helicene derivatives bearing extended π-conjugated cyano substituents

Mehdi El Sayed Moussa
, Monika Srebro
, Emmanuel Anger
, Nicolas Vanthuyne
, Christian Roussel
, Christophe Lescop
, Jochen Autschbach
, Jeanne Crassous

Chemistry

Université de Rennes
Jagiellonian University in Kraków
Aix Marseille University

Research output: Contribution to journal › Article › peer-review

35 Scopus citations

Abstract

New carbo[6]helicene derivatives grafted with π-conjugated cyano-phenyl arms were synthesized in enantiopure forms and their π-conjugation examined by UV-vis spectroscopy. The influence of the π-conjugation on the circular dichroism spectra and molar rotations is discussed based on comparing experimental data with results from quantum-chemical calculations. The results highlight the fact that increasing the spatial extension of the π-system in a helicene molecule is an efficient way of increasing its molar rotation.

Original language	English
Pages (from-to)	455-465
Number of pages	11
Journal	Chirality
Volume	25
Issue number	8
DOIs	https://doi.org/10.1002/chir.22201
State	Published - Aug 2013

Keywords

circular dichroism
helicene
pi-conjugation
quantum-chemical calculations

Access to Document

10.1002/chir.22201

Cite this

@article{869b09fb563b45f784c999c3070d698f,

title = "Chiroptical properties of carbo[6]helicene derivatives bearing extended π-conjugated cyano substituents",

abstract = "New carbo[6]helicene derivatives grafted with π-conjugated cyano-phenyl arms were synthesized in enantiopure forms and their π-conjugation examined by UV-vis spectroscopy. The influence of the π-conjugation on the circular dichroism spectra and molar rotations is discussed based on comparing experimental data with results from quantum-chemical calculations. The results highlight the fact that increasing the spatial extension of the π-system in a helicene molecule is an efficient way of increasing its molar rotation.",

keywords = "circular dichroism, helicene, pi-conjugation, quantum-chemical calculations",

author = "Moussa, \{Mehdi El Sayed\} and Monika Srebro and Emmanuel Anger and Nicolas Vanthuyne and Christian Roussel and Christophe Lescop and Jochen Autschbach and Jeanne Crassous",

year = "2013",

month = aug,

doi = "10.1002/chir.22201",

language = "English",

volume = "25",

pages = "455--465",

journal = "Chirality",

issn = "0899-0042",

publisher = "Wiley-Liss Inc.",

number = "8",

}

TY - JOUR

T1 - Chiroptical properties of carbo[6]helicene derivatives bearing extended π-conjugated cyano substituents

AU - Moussa, Mehdi El Sayed

AU - Srebro, Monika

AU - Anger, Emmanuel

AU - Vanthuyne, Nicolas

AU - Roussel, Christian

AU - Lescop, Christophe

AU - Autschbach, Jochen

AU - Crassous, Jeanne

PY - 2013/8

Y1 - 2013/8

N2 - New carbo[6]helicene derivatives grafted with π-conjugated cyano-phenyl arms were synthesized in enantiopure forms and their π-conjugation examined by UV-vis spectroscopy. The influence of the π-conjugation on the circular dichroism spectra and molar rotations is discussed based on comparing experimental data with results from quantum-chemical calculations. The results highlight the fact that increasing the spatial extension of the π-system in a helicene molecule is an efficient way of increasing its molar rotation.

AB - New carbo[6]helicene derivatives grafted with π-conjugated cyano-phenyl arms were synthesized in enantiopure forms and their π-conjugation examined by UV-vis spectroscopy. The influence of the π-conjugation on the circular dichroism spectra and molar rotations is discussed based on comparing experimental data with results from quantum-chemical calculations. The results highlight the fact that increasing the spatial extension of the π-system in a helicene molecule is an efficient way of increasing its molar rotation.

KW - circular dichroism

KW - helicene

KW - pi-conjugation

KW - quantum-chemical calculations

UR - https://www.scopus.com/pages/publications/84880421804

U2 - 10.1002/chir.22201

DO - 10.1002/chir.22201

M3 - Article

AN - SCOPUS:84880421804

SN - 0899-0042

VL - 25

SP - 455

EP - 465

JO - Chirality

JF - Chirality

IS - 8

ER -

Chiroptical properties of carbo[6]helicene derivatives bearing extended π-conjugated cyano substituents

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this