Preparation of a Rigid and Nearly Coplanar Bis-tetracene Dimer through an Application of the CANAL Reaction

Ethan G. Miller; Madhu Singh; Sean Parkin; Tarek Sammakia; Niels H. Damrauer

doi:10.1021/acs.joc.3c00809

Preparation of a Rigid and Nearly Coplanar Bis-tetracene Dimer through an Application of the CANAL Reaction

Ethan G. Miller
, Madhu Singh
, Sean Parkin
, Tarek Sammakia
, Niels H. Damrauer

Chemistry

Producción científica: Article › revisión exhaustiva

7 Citas (Scopus)

Resumen

A rigid tetracene dimer with a substantial interchromophore distance has been prepared through an application of the recently developed catalytic arene-norbornene annulation (CANAL) reaction. An iterative cycloaddition route was found to be unsuccessful, so a shorter route was adopted whereby fragments were coupled in the penultimate step to form a 13:1 mixture of two diastereomers, the major of which was isolated and crystallized. Constituent tetracene moieties are linked with a rigid, well-defined bridge and feature a near-co-planar mutual orientation of the acenes.

Idioma original	English
Páginas (desde-hasta)	12251-12256
Número de páginas	6
Publicación	Journal of Organic Chemistry
Volumen	88
N.º	17
DOI	https://doi.org/10.1021/acs.joc.3c00809
Estado	Published - sept 1 2023

Nota bibliográfica

Publisher Copyright:
© 2023 American Chemical Society.

Financiación

This work was funded by the United States Department of Energy, Office of Basic Energy Sciences (ERW7404), and the National Science Foundation (CHE-2102713). The authors thank Laura Maurer of CU Boulder for her preliminary efforts to collect a suitable single crystal X-ray diffraction data set. This work utilized the Alpine high-performance computing resource at the University of Colorado Boulder. Alpine is jointly funded by the University of Colorado Boulder, the University of Colorado Anschutz, Colorado State University, and the National Science Foundation (award 2201538). We also thank Arindam Sau for assistance in setting up computational jobs.

Financiadores	Número del financiador
Laura Maurer of CU Boulder
University of Colorado Anschutz Medical Campus
National Science Foundation (NSF)	CHE-2102713
Michigan State University-U.S. Department of Energy (MSU-DOE) Plant Research Laboratory
Office of Basic Energy Sciences	ERW7404
Colorado State University Extension	2201538
University of Colorado Boulder

ASJC Scopus subject areas

Organic Chemistry

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abstract = "A rigid tetracene dimer with a substantial interchromophore distance has been prepared through an application of the recently developed catalytic arene-norbornene annulation (CANAL) reaction. An iterative cycloaddition route was found to be unsuccessful, so a shorter route was adopted whereby fragments were coupled in the penultimate step to form a 13:1 mixture of two diastereomers, the major of which was isolated and crystallized. Constituent tetracene moieties are linked with a rigid, well-defined bridge and feature a near-co-planar mutual orientation of the acenes.",

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doi = "10.1021/acs.joc.3c00809",

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AU - Miller, Ethan G.

AU - Singh, Madhu

AU - Parkin, Sean

AU - Sammakia, Tarek

AU - Damrauer, Niels H.

PY - 2023/9/1

Y1 - 2023/9/1

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AB - A rigid tetracene dimer with a substantial interchromophore distance has been prepared through an application of the recently developed catalytic arene-norbornene annulation (CANAL) reaction. An iterative cycloaddition route was found to be unsuccessful, so a shorter route was adopted whereby fragments were coupled in the penultimate step to form a 13:1 mixture of two diastereomers, the major of which was isolated and crystallized. Constituent tetracene moieties are linked with a rigid, well-defined bridge and feature a near-co-planar mutual orientation of the acenes.

UR - https://www.scopus.com/pages/publications/85169900340

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JF - Journal of Organic Chemistry

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ER -

Preparation of a Rigid and Nearly Coplanar Bis-tetracene Dimer through an Application of the CANAL Reaction

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