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Paper | Regular issue | Vol 71, No. 9, 2007, pp.2003-2010
Published online, 8th June, 2007
DOI: 10.3987/COM-07-11094
Synthesis and Properties of 3,2’-Polymethylene-2-phenylbenzo[b]-1,10-phenanthrolines

A. F. M. Motiur Rahman and Yurngdong Jahng*

*College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Korea

Abstract

Reactions of 4-aminoacridine-3-carbaldehyde with benzo[b]cycloalkanones and 3,4-dihydro-1(2H)-anthracenone afforded a series of corresponding 3,2’-polymethylene-2-phenylbenzo[b]-1,10-phenanthrolines and 3,3’-dimethylene-2-(naphth-2’-yl)benzo[b]-1,10-phenanthroline, respectively, as new N,N,C-terdentates. Dehydrogenation of dimethylene-bridged systems afforded the corresponding fully aromatized systems. Flexibility of annulated bridges is highly dependent on the length of the carbon chain, where tetramethylene-bridge is rigid enough to differentiate eight bridge protons in 1H NMR time scale at room temperature.