The Structural Origins of Intense Circular Dichroism in a Waggling Helicene Nanoribbon

Schuster, Nathaniel J.; Joyce, Leo A.; Paley, Daniel W.; Ng, Fay; Steigerwald, Michael L.; Nuckolls, Colin

doi:10.1021/jacs.0c00646

The Structural Origins of Intense Circular Dichroism in a Waggling Helicene Nanoribbon

Journal Article · Fri Apr 03 00:00:00 EDT 2020 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.0c00646· OSTI ID:2202956

Schuster, Nathaniel J. ^[1]; ^[2]; Paley, Daniel W. ^[3]; Ng, Fay ^[3]; Steigerwald, Michael L. ^[3]; ^[3]

Columbia University, New York, NY (United States); Columbia University
Merck and Co., Inc., Rahway, NJ (United States); Arrowhead Pharmaceuticals, Madison, WI (United States)
Columbia University, New York, NY (United States)

We report the synthesis of a new perylene-diimide-based helical nanoribbon, which exhibits the largest molar electronic circular dichroism in the visible range of any molecule. Here, this nanoribbon also displays a substantial increase in molar circular dichroism relative to a smaller helical analogue, even though they share a similar structure: both nanoribbons incorporate two conformationally dynamic double-[4]helicene termini and a rigid [6]helicene-based core within their helical superstructures. Using DFT and TDDFT calculations, we find that the double-[4]helicenes within both nanoribbons orient similarly in solution; as such, conformational differences do not account for the disparities in circular dichroism. Instead, our results implicate the configuration of the double-[6]helicene within the larger nanoribbon as the source of the observed chiroptical amplification.

View Accepted Manuscript (DOE)

Research Organization:: Columbia University, New York, NY (United States)

Sponsoring Organization:: USDOE; U.S. Office of Naval Research

Grant/Contract Number:: SC0019440

OSTI ID:: 2202956

Alternate ID(s):: OSTI ID: 1803820

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 15 Vol. 142; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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