2008
DOI: 10.1016/j.tet.2008.07.043
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Synthesis and characterization of novel (oligo)thienyl-imidazo-phenanthrolines as versatile π-conjugated systems for several optical applications

Abstract: New thermally stable heterocyclic chromophores 3-6 based on a (oligo)thiophene πconjugated bridge and a imidazo-phenanthroline moiety were synthesized in moderate to excellent yields by condensation of 5,6-phenanthroline-dione with formyl (oligo)thiophenes 1-2 in the presence of ammonium acetate in glacial acetic acid.

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Cited by 86 publications
(47 citation statements)
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“…Spectra obtained for the diruthenium complexes showed both acetone and water signals, and elemental analysis data matched better with predicted formulas when these solvents were considered. This observation has been reported for similar polynuclear compounds crystallized from mixed-solvent systems [20]. Fig.…”
Section: H Nmr Spectrasupporting
confidence: 87%
“…Spectra obtained for the diruthenium complexes showed both acetone and water signals, and elemental analysis data matched better with predicted formulas when these solvents were considered. This observation has been reported for similar polynuclear compounds crystallized from mixed-solvent systems [20]. Fig.…”
Section: H Nmr Spectrasupporting
confidence: 87%
“…Preparation of IML 3 began with lithiation and carbonylation of 2-methoxythiophene ( 26 ) in Scheme 4. 23 A Knoevenagel condensation with diethyl malonate introduced the required ester, and subsequent reduction with sodium borohydride selectively removed the reactive alkene to give diester 28 . 24,25 The esters were hydrolyzed with potassium hydroxide.…”
Section: Resultsmentioning
confidence: 99%
“…The subsequent explorations have gained an increasing prominence on the strength of their fruitful implementations such as various luminescent sensors or stimulants, pharmacological agents, photoactive materials of organic light emitting diode (OLED) devices and mesophasic ingredients of liquid crystals. More precisely imp derivatives, associated with their large Stokes shifts and luminescence lifetimes, have excellent photophysical applications such as efficient hole blocker and electron transporters in OLED materials and molecular switches [2][3][4][5][6][7][8][9]. They are available as multifunctional ligands in the construction of high order non-linear systems [10][11][12].…”
Section: Introductionmentioning
confidence: 99%