925674-61-9Relevant academic research and scientific papers
Novel chromophores from alternated pyridine-ethylenedioxythiophene unit oligomers: Dramatic enhancement of photoluminescence properties in elongated derivatives
Chevallier, Floris,Charlot, Marina,Katan, Claudine,Mongin, Florence,Blanchard-Desce, Mireille
, p. 692 - 694 (2009)
Novel chromophores based on the alternation of electron-poor (pyridyl) and electron-rich (ethylenedioxythienyl) heterocycles were synthesized for the first time and shown to exhibit attractive optical properties in relation with their specific electronic and geometrical (coiled structure) features. The Royal Society of Chemistry 2009.
Self-association in {2-[3,4-alkylenedioxy-5-(3-pyridyl)]-thienyl}alkanols: An NMR, IR, and single-crystal X-ray study
Lomas, John S.,Cordier, Christine,Adenier, Alain,Maurel, Francois,Vaissermann, Jacqueline
, p. 410 - 421 (2008/02/04)
syn-2,2,4,4-Tetramethyl-3- {2-[3,4-alkylenedioxy-5-(3-pyridyl)]thienyl} pentan-3-ols self-associate both in the solid state and in solution. Single-crystal X-ray diffraction study of the 3,4-ethylenedioxythiophene (EDOT) derivative shows that it exists as a centrosymmetric head-to-tail, syn dimer in the solid state. The IR spectra of the solids display only a broad OH absorption around 3300 cm-1, corresponding to a hydrogen-bonded species. 1H Nuclear Overhauser Effect Spectroscopy (NOESY) NMR experiments in benzene reveal interactions between the fert-butyl groups and the H2 and H6 protons of the pyridyl group. Two approaches have been used to determine association constants of the EDOT derivative by NMR titration, based on the concentration dependence of (i) the synl anti ratio and (ii) the OH proton shift of the syn rotamer. Reasonably concordant results are obtained from 298 to 323 K (3.6 and 3.9 M-1, respectively, at 298 K). Similar values are obtained from the syn OH proton shift variation for the 3,4- methylenedioxythiophene (MDOT) derivative. Concentration-dependent variation of the anti OH proton shift in the latter suggests that the anti isomer associates in the form of an open, singly hydrogen-bonded dimer, with a much smaller association constant than the syn rotamer. Self-association constants for 3-pyridyl-EDOT-alkanols with smaller substituents vary by a factor of 4 from (i-Pr)2 up to (CD3)2, while the hetero-association constants for the same compounds with pyridine vary slightly less. Copyright
Synthesis of mono- and bis-arylated 3,4-(ethylenedioxythiophenes) via direct palladium catalyzed arylation reactions
Mohanakrishnan, Arasambattu K.,Amaladass,Arul Clement
, p. 539 - 544 (2007/10/03)
The synthesis of arylated/heteroarylated 3,4-ethylenedioxythiophene derivatives is reported using a straightforward palladium mediated Heck coupling of 3,4-ethylenedioxythiophene with various aryl/heteroaryl halides.
Pd-mediated C-H arylation of EDOT and synthesis of push-pull systems incorporating EDOT
Amaladass,Clement, J. Arul,Mohanakrishnan, Arasambattu K.
, p. 10363 - 10371 (2008/02/13)
The direct C-H arylation of 3,4-ethylenedioxythiophene (EDOT) is described under Heck-type experimental conditions. This methodology has been used to synthesize a series of push-pull systems containing EDOT units.
