Self-assembly and two-dimensional spontaneous resolution of cyano-functionalized [7]helicenes on Cu(111)

Meike Stöhr; Serpil Boz; Michael Schär; Manh Thuong Nguyen; Carlo A. Pignedoli; Daniele Passerone; W. Bernd Schweizer; Carlo Thilgen; Thomas A. Jung; Franãçois Diederich

doi:10.1002/anie.201102627

Self-assembly and two-dimensional spontaneous resolution of cyano-functionalized [7]helicenes on Cu(111)

Meike Stöhr
, Serpil Boz
, Michael Schär
, Manh Thuong Nguyen
, Carlo A. Pignedoli
, Daniele Passerone
, W. Bernd Schweizer
, Carlo Thilgen
, Thomas A. Jung
, Franãçois Diederich

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

68 Scopus citations

Abstract

Birds of a feather flock together: STM and DFT studies provide the first example of spontaneous chiral resolution of a helicene on a surface. Racemic 6,13-dicyano[7]helicene forms fully segregated domains of pure enantiomers (2D conglomerate) on Cu(111). The propensity of the system to optimize intermolecular CN⋯HC(Ar) hydrogen bonding and CN⋯CN dipolar interactions translates into chiral recognition with preferential assembly of homochiral molecules.

Original language	English (US)
Pages (from-to)	9982-9986
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	42
DOIs	https://doi.org/10.1002/anie.201102627
State	Published - Oct 10 2011
Externally published	Yes

Keywords

chirality
helicenes
scanning probe microscopy
spontaneous resolution
surface-confined self-assembly

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201102627

Cite this

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title = "Self-assembly and two-dimensional spontaneous resolution of cyano-functionalized [7]helicenes on Cu(111)",

abstract = "Birds of a feather flock together: STM and DFT studies provide the first example of spontaneous chiral resolution of a helicene on a surface. Racemic 6,13-dicyano[7]helicene forms fully segregated domains of pure enantiomers (2D conglomerate) on Cu(111). The propensity of the system to optimize intermolecular CN⋯HC(Ar) hydrogen bonding and CN⋯CN dipolar interactions translates into chiral recognition with preferential assembly of homochiral molecules.",

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doi = "10.1002/anie.201102627",

language = "English (US)",

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T1 - Self-assembly and two-dimensional spontaneous resolution of cyano-functionalized [7]helicenes on Cu(111)

AU - Stöhr, Meike

AU - Boz, Serpil

AU - Schär, Michael

AU - Nguyen, Manh Thuong

AU - Pignedoli, Carlo A.

AU - Passerone, Daniele

AU - Schweizer, W. Bernd

AU - Thilgen, Carlo

AU - Jung, Thomas A.

AU - Diederich, Franãçois

PY - 2011/10/10

Y1 - 2011/10/10

N2 - Birds of a feather flock together: STM and DFT studies provide the first example of spontaneous chiral resolution of a helicene on a surface. Racemic 6,13-dicyano[7]helicene forms fully segregated domains of pure enantiomers (2D conglomerate) on Cu(111). The propensity of the system to optimize intermolecular CN⋯HC(Ar) hydrogen bonding and CN⋯CN dipolar interactions translates into chiral recognition with preferential assembly of homochiral molecules.

AB - Birds of a feather flock together: STM and DFT studies provide the first example of spontaneous chiral resolution of a helicene on a surface. Racemic 6,13-dicyano[7]helicene forms fully segregated domains of pure enantiomers (2D conglomerate) on Cu(111). The propensity of the system to optimize intermolecular CN⋯HC(Ar) hydrogen bonding and CN⋯CN dipolar interactions translates into chiral recognition with preferential assembly of homochiral molecules.

KW - chirality

KW - helicenes

KW - scanning probe microscopy

KW - spontaneous resolution

KW - surface-confined self-assembly

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AN - SCOPUS:80053901607

SN - 1433-7851

VL - 50

SP - 9982

EP - 9986

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 42

ER -

Self-assembly and two-dimensional spontaneous resolution of cyano-functionalized [7]helicenes on Cu(111)

Abstract

Keywords

ASJC Scopus subject areas

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