Cycloreversion Approach For Preparation of Large π‐Conjugated Compounds

In this study, a benzene-fused bis(thiaporphyrin) was synthesized by the retro-Diels–Alder reaction of a bicyclo[2.2.2]octadiene (BCOD)-fused bis(thiaporphyrin) precursor. This precursor was prepared by the double [3+1] porphyrin synthesis of the BCOD-fused dipyrrole with thiatripyrrane. The ultraviolet–visible (UV–vis) spectrum of benzene-fused bis(thiaporphyrin) in dichloromethane was extremely different from that of the corresponding benzene-fused bis(porphyrin). In contrast, extremely similar spectra were obtained in the presence of trifluoroacetic acid. The similar electronic structures in the protonated states were supported by X-ray analysis and time-dependent density-functional theory (TD-DFT) calculations.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Cycloreversion Approach For Preparation of Large π‐Conjugated Compounds

Cited by 2 publications

References 171 publications

Face‐ and Regioselectivity in Electrophilic Phenylsulfenylation of 7‐tert‐Butoxybicyclo[2.2.1]hepta‐2,5‐dienes

Face‐ and Regioselectivity in Electrophilic Phenylsulfenylation of 7‐tert‐Butoxybicyclo[2.2.1]hepta‐2,5‐dienes

Synthesis and Properties of Bicyclo[2.2.2]octadiene- and Benzene-Fused Bis(thiaporphyrin)s

Contact Info

Product

Resources

About