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Synthesis and Stereochemical Behavior of Dioxa[6]helicene Derivatives
Author(s) -
Shyam Sundar M.,
Lo Rabindranath,
Dračínský Martin,
Klepetářová Blanka
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202100583
Subject(s) - helicene , chemistry , cyclic voltammetry , density functional theory , crystallography , derivative (finance) , computational chemistry , stereochemistry , molecule , electrochemistry , organic chemistry , electrode , financial economics , economics
Abstract We constructed a helically chiral dioxa[6]helicene by assembling simple phenol building blocks by a combination of two simple reactions involving oxidative cross‐coupling followed by dehydrative cyclization. X‐ray analysis and density functional calculations (DFT) revealed that the compound dioxa[6]helicene has a helical structure that undergoes helical inversion rapidly at room temperature. We were able to detect the presence of resolvable helical isomers of (−)‐menthyloxycarbonyl derivative of dioxa[6]helicene by recording 1 H NMR spectra below 0 °C. The investigations of photo physical properties by cyclic voltammetry, UV/Vis‐ and fluorescence properties with the aid of time‐dependent DFT calculations were undertaken.