TY - JOUR
T1 - Preparation of a Rigid and Nearly Coplanar Bis-tetracene Dimer through an Application of the CANAL Reaction
AU - Miller, Ethan G.
AU - Singh, Madhu
AU - Parkin, Sean
AU - Sammakia, Tarek
AU - Damrauer, Niels H.
N1 - Publisher Copyright:
© 2023 American Chemical Society.
PY - 2023/9/1
Y1 - 2023/9/1
N2 - 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.
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 - http://www.scopus.com/inward/record.url?scp=85169900340&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85169900340&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.3c00809
DO - 10.1021/acs.joc.3c00809
M3 - Article
AN - SCOPUS:85169900340
SN - 0022-3263
VL - 88
SP - 12251
EP - 12256
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -