Abstract

The extension of π-conjugation of polycyclic aromatic hydrocarbons (PAHs) via alkyne benzannulation reactions has become an increasingly utilized tool over the past few years. This short review will highlight recent work of alkyne benzannulations in the context of large nanographene as well as graphene nanoribbon synthesis along with a brief discussion of the interesting physical properties these molecules display.

Highlights

  • The term “nanographenes (NGs)” has recently become a popular term used to describe relatively large polycyclic aromatic hydrocarbons (PAHs) [1]

  • Iodine Monochloride (ICl)-induced benzannulation used in the synthesis towards dibenzo[g,p]chrysene derivatives

  • Electrophilic iodine-mediated alkyne benzannulations have proven to be an excellent tool for Electrophilic iodine-mediated alkyne benzannulations have proven to be an excellent tool for the synthesis of functionalized nanographenes

Read more

Summary

Introduction

The term “nanographenes (NGs)” has recently become a popular term used to describe relatively large polycyclic aromatic hydrocarbons (PAHs) [1] These molecules represent discrete sections of graphene, a material with its own interesting chemical and physical properties [2,3]. The development of bottom-up synthetic tools for the production of GNRs has been an area of recent interest for the purpose of imparting solubility and tuning of the material properties. This short review will discuss the state of the art for NG and GNR synthesis with a focus on alkyne benzannulations [16] as the key chemical transformation

Alkyne Benzannulations via Pyrolysis
Alkyne Benzannulatinos via Photocyclizations
Alkyne Benzannulations Promoted by Electrophilic Reagents
BF4 as an electrophilic developed in 1988ofbyTfOH
Synthetic
Radical-mediated
Acid-mediated Alkyne Benzannulations
Brønsted Acid Catalyzed Alkyne Benzannulations
Brønsted acid-promoted and four-fold alkyne benzannulations to afford pyrenes
X-ray crystal structures of peropyrene
53. The X-ray structure shows this molecule to be twisted
12. Soluble GNRalkyne
Transition Metal-Catalyzed Cyclizations
14. Synthesis
InCl steps using
Main Group π-Lewis Acid-Catalyzed Cyclizations
Base-mediated
Findings
Conclusions

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call

Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.