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Synthesis and Redox Behavior of Novel 9,10‐Diphenylphenanthrenes
Author(s) -
Schreivogel Alina,
Sieger Monika,
Baro Angelika,
Laschat Sabine
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000238
Subject(s) - chemistry , redox , cyclic voltammetry , electrolyte , electrochemistry , solvent , substituent , supporting electrolyte , oxidation process , phenanthrene , derivative (finance) , inorganic chemistry , photochemistry , medicinal chemistry , electrode , organic chemistry , chemical engineering , economics , financial economics , engineering
The synthesis and electrochemical investigations of 9,10‐diphenylphenanthrene 2a and its derivatives 2b – 2e are reported. The cyclic voltammetry of derivatives 2a – 2c and 2e in different solvent/Bu 4 NPF 6 electrolyte systems reveals that the redox properties are dependent on solvent, temperature, and sweep rate. The oxidation of 9,10‐diphenylphenanthrene 2a occurred as an irreversible process, while two fully reversible oxidation waves were observed for dimethoxy derivative 2c . The room‐temperature oxidation of brominated compound 2b is reversible, whereas AcO‐substituted phenanthrene 2e displayed a reversible oxidation peak only at low temperature. Furthermore, the electronic nature of the substituent affects the oxidation potentials. In the CH 2 Cl 2 ‐based electrolyte system, the first oxidation potentials increase in the order 2c < 2e < 2b .