Synthesis of Substituted Trinaphthylenes

Area of Science:

• Organic Chemistry
• Supramolecular Chemistry
• Materials Science

Background:

• Cyclotrinaphthylenes are polycyclic aromatic hydrocarbons with potential applications in materials science.
• The synthesis and structural characterization of alkoxy-substituted derivatives are crucial for understanding their properties.
• Previous studies have not described the crystal structures of these specific trinaphthylene derivatives.

Purpose of the Study:

• To synthesize a series of six novel alkoxy-substituted cyclotrinaphthylenes.
• To investigate the crystal packing patterns of these synthesized compounds using single-crystal X-ray diffraction.
• To report the hitherto undescribed crystal structures of these trinaphthylene derivatives.

Main Methods:

• Yamamoto-type coupling reaction using Ni(COD)2 as a catalyst.
• Synthesis of six cyclotrinaphthylene derivatives with varying alkoxy substituents (OHex, OBu, OiPr, OPr, OEt, OMe).
• Single-crystal X-ray structure determination to analyze packing patterns.

Main Results:

• Successful synthesis of six alkoxy-substituted cyclotrinaphthylenes with yields ranging from 38% to 65%.
• Demonstration of different packing patterns adopted by the cyclotrinaphthylenes based on their specific structures.
• Obtained and described the crystal structures of these novel trinaphthylene compounds for the first time.

Conclusions:

• The Yamamoto-type coupling provides an effective route to alkoxy-substituted cyclotrinaphthylenes.
• The alkoxy substituents influence the solid-state packing arrangements of these molecules.
• The reported crystal structures provide a foundation for future studies on the properties and applications of cyclotrinaphthylenes.