Diels-Alder Additions to 2,2’-Biaceanthrylene

28 April 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A series of Diels-Alder reactions between the diene 2,2’-biaceanthylene and several dienophiles is presented. The diene is a cyclopenta-fused polycyclic aromatic hydrocarbon with anthracene units linked by two cyclopentene rings. Depending on the dienophile, the major product was the result of a single addition (dimethyl acetylenedicarboxylate) or double addition (quinone, benzyne) to the diene. Single crystal X-ray analysis of the quinone-derivative shows a propeller-like structure composed of mixed enantiomers. The synthesis and photophysical properties of these compounds is presented.


Diels-Alder Reaction
cyclopentannulated polycyclic aromatic hydrocarbon
polycyclic aromatic hydrocarbon

Supplementary materials

Supporting information Diels-Alder to CP-PAH 04-24-21


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.