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Modified expanded corrole-ferrocene conjugates: syntheses, structure and properties.

Rajeev Kumar¹, Rajneesh Misra, Viswanathan PrabhuRaja

¹Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|July 22, 2005

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New expanded corrole-ferrocene conjugates were synthesized and characterized. Their optical, electronic, and structural properties were investigated, revealing tunable characteristics based on spacer groups and direct linkage, impacting their potential applications.

Area of Science:

Organic Chemistry
Materials Science
Supramolecular Chemistry

Background:

Corroles and ferrocenes are important organic molecules with unique electronic and optical properties.
Expanded porphyrin systems, like corroles, offer tunable photophysical characteristics.
Ferrocene-containing conjugates are of interest for their redox activity and potential in molecular electronics.

Purpose of the Study:

To synthesize and characterize novel expanded corrole-ferrocene conjugates with varying spacer groups.
To investigate the influence of spacer groups and linkage position on the optical, emission, and electrochemical properties.
To explore the potential of these conjugates in nonlinear optics and metal complexation.

Main Methods:

Synthesis of ferrocene-spacer units followed by "3+2" acid-catalyzed oxidative coupling.

Related Experiment Videos

Characterization using optical absorption, emission spectroscopy, single crystal X-ray diffraction, and electrochemical methods.

Measurement of molecular first hyperpolarizabilities (beta) using Hyper-Rayleigh Scattering (HRS).

Main Results:

Successful synthesis of expanded corrole-ferrocene conjugates with three different spacer groups.
Optical and emission properties are dependent on spacer nature and length, with direct linkage showing maximum effects.
X-ray structures reveal C-C bond shortening, indicating electronic interaction between corrole and ferrocene pi systems.
Electrochemical data show electron-donating nature of ferrocene and easier corrole oxidation, influenced by spacer length.
Nonlinear optical properties (beta values) range from 20-32x10(-30) esu, suggesting potential for enhancement.
Formation of 1:1 Rh(I) metal complexes.

Conclusions:

The study demonstrates a versatile synthetic route to expanded corrole-ferrocene conjugates.
Spacer engineering allows for tuning of photophysical and electrochemical properties.
These conjugates exhibit promising nonlinear optical behavior and metal-binding capabilities.