Ferrocene-isocoumarin conjugated molecules: synthesis, structural characterization, electronic properties, and...

Area of Science:

• Organic Chemistry
• Materials Science
• Computational Chemistry

Background:

• Ferrocene and isocoumarin derivatives are valuable building blocks in organic synthesis.
• Conjugated organic molecules are crucial for developing advanced electronic and optical materials.
• Understanding structure-property relationships is key to designing novel functional materials.

Purpose of the Study:

• To synthesize novel ferrocene-isocoumarin conjugated molecules.
• To investigate the structural, optical, and electrochemical properties of these new compounds.
• To compare the properties of the synthesized molecules with their precursors.

Main Methods:

• Synthesis via acid-prompted regioselective oxidative cyclization.
• Structural characterization using single-crystal X-ray diffraction.
• Computational analysis using density functional theory (DFT) and time-dependent DFT (TDDFT).
• Electrochemical property evaluation using cyclic voltammetry (CV).

Main Results:

• Two ferrocene-isocoumarin compounds were successfully synthesized.
• The synthesized compounds exhibit improved coplanarity compared to their precursors.
• UV-visible spectroscopy revealed characteristic electronic transitions (MLCT, ICT, π-π*) with higher oscillator strength in the products.
• Cyclic voltammetry confirmed electrochemical properties consistent with theoretical calculations.

Conclusions:

• The acid-prompted cyclization is an effective method for synthesizing ferrocene-isocoumarin conjugates.
• Enhanced coplanarity in the synthesized molecules influences their optical properties.
• The study provides valuable insights into the structure-property relationships of ferrocene-based conjugated systems.