Literature DB >> 33034405

Carbo[n]helicenes Restricted to Enantiomerize: An Insight into the Design Process of Configurationally Stable Functional Chiral PAHs.

Prince Ravat1.   

Abstract

The most important stereodynamic feature of carbo[n]helicenes is the interconversion of their enantiomers. The Gibbs activation energy (ΔG≠ (T)) of this process, which determines the rate of enantiomerization, dictates the configurational stability of [n]helicenes. High values of ΔG≠ (T) are required for applications of functional chiral molecules incorporating [n]helicenes or helicene substructures. This minireview provides an overview of the mechanism, recent developments, and factors affecting the enantiomerization of [n]helicenes, which will accelerate the design process of configurationally stable functional chiral molecules based on helicene substructures. Additionally, this minireview addresses the misconception and irregularities in the recent literature on how the terms "racemization" and "enantiomerization" are used as well as how the activation parameters are calculated for [n]helicenes and related compounds.
© 2020 The Authors. Published by Wiley-VCH GmbH.

Entities:  

Keywords:  Gibbs activation energy; [n]helicenes; configurational stability; enantiomerization; racemization

Year:  2020        PMID: 33034405     DOI: 10.1002/chem.202004488

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  3 in total

1.  Enhanced N-directed electrophilic C-H borylation generates BN-[5]- and [6]helicenes with improved photophysical properties.

Authors:  Kang Yuan; Daniel Volland; Sven Kirschner; Marina Uzelac; Gary S Nichol; Agnieszka Nowak-Król; Michael J Ingleson
Journal:  Chem Sci       Date:  2022-01-04       Impact factor: 9.825

2.  Theoretical Prediction of Structures, Vibrational Circular Dichroism, and Infrared Spectra of Chiral Be4B8 Cluster at Different Temperatures.

Authors:  Carlos Emiliano Buelna-García; Eduardo Robles-Chaparro; Tristan Parra-Arellano; Jesus Manuel Quiroz-Castillo; Teresa Del-Castillo-Castro; Gerardo Martínez-Guajardo; Cesar Castillo-Quevedo; Aned de-León-Flores; Gilberto Anzueto-Sánchez; Martha Fabiola Martin-Del-Campo-Solis; Ana Maria Mendoza-Wilson; Alejandro Vásquez-Espinal; Jose Luis Cabellos
Journal:  Molecules       Date:  2021-06-28       Impact factor: 4.411

3.  Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π-Scaffold.

Authors:  Ben Teichmann; Ana-Maria Krause; Mei-Jin Lin; Frank Würthner
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-18       Impact factor: 16.823

  3 in total

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