A BN-Doped Cycloparaphenylene Debuts.

Area of Science:

• Organic Chemistry
• Materials Science
• Supramolecular Chemistry

Background:

• Cycloparaphenylenes (CPPs) are a unique class of molecular nanocarbons.
• Functionalization of CPPs is challenging, limiting their applications.
• Boron nitride (BN) doping offers a route to modify electronic properties of organic scaffolds.

Purpose of the Study:

• To synthesize and characterize the first BN-doped cycloparaphenylene (BN-[10]CPP).
• To investigate the reactivity and photophysical properties of BN-[10]CPP in comparison to carbon analogues.
• To explore the potential for late-stage functionalization of BN-doped CPPs.

Main Methods:

• Synthesis of BN-[10]CPP.
• Characterization using spectroscopic and analytical techniques.
• Comparative evaluation of reactivity and photophysical properties against Mes-[10]CPP and [10]CPP.
• Iridium-catalyzed hydrogenation and subsequent hydrolysis.

Main Results:

• Successful synthesis and characterization of BN-[10]CPP.
• BN-[10]CPP exhibits similar photophysical properties to carbonaceous CPPs.
• The BN heterocycle enables facile and selective late-stage functionalization.
• Selective reduction of the BN ring followed by hydrolysis yielded a macrocyclic ketone.

Conclusions:

• The introduction of a BN heterocycle into the CPP scaffold significantly alters its electronic structure.
• BN-doping facilitates selective chemical transformations not achievable with traditional CPPs.
• This work provides a new method for synthesizing complex macrocyclic structures containing ketone functionalities.