Literature DB >> 30853851

Enantiomerically Pure 5,13-Dicyano-9-oxa[7]helicene: Synthesis and Study.

Riddhi Gupta1, Trevor A Cabreros2, Gilles Muller2, Ashutosh V Bedekar1.   

Abstract

Optically pure dicyano oxa[7]helicenes and helicene-like molecules have been prepared and investigated for their optical behavior. The isomers of the intermediate 4,4'-biphen-anthrene-3,3'-diol were resolved by physically separating their 1-menthyl carbonate derivatives. In this work a mild method was developed to cleave ArOMe in presence of a cyano group. The optical rotation of atropisomeric diol, helicenes-like compounds and the oxa[7]helicenes was observed to be in increasing order, while the molecules also showed good response to circularly polarized luminescence.

Entities:  

Keywords:  Atropisomers; Helicenes; Luminescence; Photophysical properties

Year:  2018        PMID: 30853851      PMCID: PMC6402497          DOI: 10.1002/ejoc.201800922

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  57 in total

1.  F8BINOL, an electronically perturbed version of BINOL with remarkable configurational stability

Authors: 
Journal:  Org Lett       Date:  2000-01       Impact factor: 6.005

2.  New rigid angular dicarboxylic acid for the construction of nanoscopic supramolecules: from a molecular rectangle to a 1-D coordination polymer.

Authors:  Yong Cui; Helen L Ngo; Wenbin Lin
Journal:  Inorg Chem       Date:  2002-03-11       Impact factor: 5.165

3.  Chiral discrimination in hydrogen-bonded

Authors: 
Journal:  Org Lett       Date:  2000-10-05       Impact factor: 6.005

4.  (P)-helicene displays chiral selection in binding to Z-DNA.

Authors:  Yan Xu; You Xin Zhang; Hiroshi Sugiyama; Tomoko Umano; Hideji Osuga; Kazuhiko Tanaka
Journal:  J Am Chem Soc       Date:  2004-06-02       Impact factor: 15.419

5.  Stereospecific synthesis of hetero[7]helicenes by Pd-catalyzed double N-arylation and intramolecular O-arylation.

Authors:  Koji Nakano; Yuko Hidehira; Keita Takahashi; Tamejiro Hiyama; Kyoko Nozaki
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-04       Impact factor: 15.336

6.  Dual modulation of a molecular switch with exceptional chiroptical properties.

Authors:  Zhi Yuan Wang; Erin K Todd; Xian Sheng Meng; Jian Ping Gao
Journal:  J Am Chem Soc       Date:  2005-08-24       Impact factor: 15.419

7.  7:8,9:10-dibenzo-1,2,3,4-tetrafluoro- triphenylene: synthesis, structure, and photophysical properties of a novel [5]helicene.

Authors:  Darryl J Morrison; Tyler K Trefz; Warren E Piers; Robert McDonald; Masood Parvez
Journal:  J Org Chem       Date:  2005-06-24       Impact factor: 4.354

8.  Recent developments in the synthesis of helicene-like molecules.

Authors:  Antonio Urbano
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-05       Impact factor: 15.336

9.  Circularly polarized luminescence from bridged triarylamine helicenes.

Authors:  Jason E Field; Gilles Muller; James P Riehl; D Venkataraman
Journal:  J Am Chem Soc       Date:  2003-10-01       Impact factor: 15.419

10.  Chiral recognition in the binding of helicenediamine to double strand DNA: interactions between low molecular weight helical compounds and a helical polymer.

Authors:  Shinobu Honzawa; Hitoshi Okubo; Shuzo Anzai; Masahiko Yamaguchi; Kohei Tsumoto; Izumi Kumagai
Journal:  Bioorg Med Chem       Date:  2002-10       Impact factor: 3.641

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