Issue 30, 2024

Helically twisted nanoribbons via stereospecific annulative π-extension reaction employing [7]helicene as a molecular wrench

Abstract

Over the past decade, significant progress has been made in synthesizing atomically precise carbon nanostructures, particularly graphene nanoribbons (NRs), employing advanced synthetic methodologies. Despite these advancements, achieving control over the stereochemistry of twisted NRs has proven to be a formidable challenge. This manuscript presents a strategic approach to achieve absolute control over the single-handed helical conformation in a cove-edged NR. This strategy leverages enantiopure helicenes as a molecular wrench, intricately influencing the overall conformation of the NR. [7]helicenes stitched to the terminal K-regions of a conjugated pyrene NR through a stereospecific annulative π-extension reaction to produce a helically twisted NR with an end-to-end twist of 171°. Furthermore, a detailed investigation of the impact of twisting on the conformational population was studied by quantum chemical calculations.

Graphical abstract: Helically twisted nanoribbons via stereospecific annulative π-extension reaction employing [7]helicene as a molecular wrench

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Article information

Article type
Edge Article
Submitted
18 Mar 2024
Accepted
15 May 2024
First published
23 May 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 11737-11747

Helically twisted nanoribbons via stereospecific annulative π-extension reaction employing [7]helicene as a molecular wrench

A. Swain, K. Radacki, H. Braunschweig and P. Ravat, Chem. Sci., 2024, 15, 11737 DOI: 10.1039/D4SC01814A

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