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.
| Original language | English |
|---|---|
| Pages (from-to) | 12251-12256 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 88 |
| Issue number | 17 |
| DOIs | |
| State | Published - Sep 1 2023 |
Bibliographical note
Publisher Copyright:© 2023 American Chemical Society.
Funding
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.
| Funders | Funder number |
|---|---|
| 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