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DOI: 10.1055/s-0040-1718934
A Theoretical Study on the Macrocyclic Strain of Zigzag Molecular Belts
Funding Information We thank the National Science Foundation of China (grant No. 21732004 and 21821001) and Tsinghua University Initiative Scientific Research Program for financial support.
Abstract
Zigzag molecular belts have captured the imagination of scientists for over a half century because of their aesthetically appealing structures and tantalizing properties. One of the formidable challenges in synthesis is to circumvent the energy accumulated in the construction of strained structures. Reported herein is our theoretical study to quantify the molecular strain energies. A general exponential function equation E strain = a·n·e −n/b was obtained to estimate strain energies of both conjugated and partially hydrogenated hydrocarbon belts and their heteroatom-embedded analogs. The deformation of aromatic rings from planarity was revealed to contribute dominantly to the high strain energies. The method enabled the convenient quantification of the energetics of aromatization processes from partially hydrogenated double-stranded macrocycles, and facilitated the design and optimization of practical routes to synthesize the long-awaited zigzag molecular belts.
Supporting Information
Supporting information for this article is available online at http://doi.org/10.1055/s-0040-1718934. It shows detailed calculation results.
Primary Data
- Primary Data
Primary data including the Cartesian coordinates for this article are available online at: http://doi.org/10.1055/s-0040-1718934 and can be cited using the following DOI: 10.4125/pd0123th.
Publication History
Received: 24 August 2020
Accepted: 14 September 2020
Article published online:
22 November 2020
© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).
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