Investigation of synthetic methods for preparation of 2^o-amino derivatives of 5-amino- 1, 10-phenanthroline: Applications to Cu⁺² based impedance sensors

Author

Satish B. Chunchu

Date Approved

2011

Degree Type

Open Access Thesis

Degree Name

Master of Science (MS)

Department or School

Chemistry

Committee Member

Donald Snyder, PhD, Chair

Committee Member

Timothy Friebe, PhD

Committee Member

Gregg Wilmes, PhD

Abstract

The main purpose of this project is to synthesize 2^o - derivatives of 5-amino-1, 10- phenanthroline (5-aphen) for application as self-assembled monolayers on gold interdigitated electrode array chips in standard impedance and impedance resonance-based Cu²⁺ sensors. Potential applications include monitoring Cu²⁺ leaching from anti-fouling coatings on ship hulls. The importance of the planned secondary alkyl amino derivatives will be to test their binding properties to the gold surface through dithiocarbamate linkages by monitoring the IDE impedance signal. Practical sensor development requires good impedance response, maximum binding to the gold IDE chip, and maximum long term stability of the SAM, which provides the transducer element with sensitivity, selectivity, and reproducibility. In research work, three different synthetic routes were investigated for preparation of secondary N-alkyl 5-aphen derivatives. KI- catalyzed mono alkylation of 5-aphen with alkyl halides gave significantly better results than Pd/C catalyzed mono N-alkylation with aldehydes and alkylation of 5-aphen with the PPh3/DDQ system.

Recommended Citation

Chunchu, Satish B., "Investigation of synthetic methods for preparation of 2^o-amino derivatives of 5-amino- 1, 10-phenanthroline: Applications to Cu⁺² based impedance sensors" (2011). Master's Theses and Doctoral Dissertations. 347.
https://commons.emich.edu/theses/347