Subphthalocyanine-dehydro[18]annulenes.

Area of Science:

• Organic Chemistry
• Supramolecular Chemistry
• Materials Science

Background:

• Subphthalocyanines are valuable macrocyclic compounds with unique electronic properties.
• Annulene frameworks offer rigid structures for building complex molecular architectures.

Purpose of the Study:

• To synthesize a novel subphthalocyanine trimer incorporating a dehydro[18]annulene core.
• To investigate the feasibility of using palladium-catalyzed cross-coupling and homocoupling for constructing such complex macrocycles.
• To explore the electrochemical characteristics of the newly synthesized trimers.

Main Methods:

• Synthesis of an ortho-diethynyl-functionalized subphthalocyanine via Sonogashira coupling.
• Palladium-catalyzed homocoupling of the ethynyl-functionalized subphthalocyanine to form the dehydro[18]annulene-templated trimer.
• Characterization using spectroscopic and analytical techniques.
• Electrochemical property investigation using cyclic voltammetry.

Main Results:

• Successful preparation of a subphthalocyanine trimer centered on a dehydro[18]annulene core.
• Demonstration that dehydro[12]annulene analogues do not form under similar homocoupling conditions.
• Full characterization and electrochemical analysis of the synthesized trimers were completed.

Conclusions:

• The study successfully established a synthetic route to dehydro[18]annulene-based subphthalocyanine trimers.
• The findings highlight the importance of the annulene core size in directing the outcome of homocoupling reactions.
• The synthesized trimers possess distinct electrochemical properties, suggesting potential applications in molecular electronics or photonics.