235-93-8Relevant articles and documents
Porphyrins with exocyclic rings. 13. Synthesis and spectroscopic characterization of highly modified porphyrin chromophores with fused acenaphthylene and benzothiadiazole rings
Lash, Timothy D.,Chandrasekar, Pushpa,Osuma, Augustine T.,Chaney, Sun T.,Spence, John D.
, p. 8455 - 8469 (1998)
As part of a survey on the influence of fused aromatic rings on the porphyrin chromophore, a series of novel structures with fused acenaphthylene or benzothiadiazole rings have been synthesized. Base-catalyzed condensation of 1-nitroacenaphthylene or 4-nitrobenzothiadiazole with esters of isocyanoacetic acid afforded good yields of the annelated pyrroles 5 and 28. Cleavage of the ester moieties with KOH in refluxing ethylene glycol gave the unsubstituted heterocycles, and subsequent condensation with 2 equiv of acetoxymethylpyrroles 9 in acetic acid/ethanol produced the modified tripyrranes 12 and 31. Tripyrranes with terminal tert-butyl ester units were treated with TFA and condensed with 3,4-diethyl-2,5-pyrroledicarboxaldehyde 13 in dichloromethane to give, following oxidation with DDQ, the corresponding π-extended porphyrins 14 and 32. Acenaphthoporphyrins 14 showed unique UV-vis spectra with a triply split Soret band region and a relatively strong band near 660 nm. Strongly red-shifted absorptions were also noted for the dications and the nickel(II), copper(II), and zinc chelates for this system. Thiadiazoloporphyrins 32 gave two broadened Soret bands, but the Q-band region was unexceptional. However, the nickel(II), copper(II), and zinc complexes all showed abnormally strong absorptions between 600 and 612 nm. Porphyrins with two antipodal fused aromatic rings were easily prepared by condensing c-annelated pyrroledialdehydes 17 with tripyrranes 12 and 31, and the spectroscopic properties of the resulting porphyrins showed that the observed ring-fusion effects were essentially additive. Porphyrins with two adjacent acenaphthylene rings were also prepared by the MacDonald '2 + 2' condensation, although this chemistry gave poor results in the synthesis of a porphyrin with two fused benzothiadiazole rings. The spectroscopic properties of these new highly conjugated porphyrin structures show that ring fusion can profoundly modify the porphyrin chromophore.
Synthesis of Pyrroles annulated with Polycyclic Aromatic Compounds; Precursor Molecules for Low Band Gap Polymers
Ono, Noboru,Hironaga, Hideo,Simizu, Kazuhiro,Ono, Kazuo,Kuwano, Kayoko,Ogawa, Takuji
, p. 1019 - 1020 (1994)
Pyrroles annulated with polycyclic aromatic compounds, which are expected to be good precursor molecules for low band gap polymers, are prepared by the reaction of aromatic nitro compounds with ethyl isocyanoacetate and the subsequent deethoxycarbonylation.
Synthesis and spectroscopic characterization of meso-tetraarylporphyrins with fused phenanthrene rings
Xu, Hai-Jun,Shen, Zhen,Okujima, Tetsuo,Ono, Noboru,You, Xiao-Zeng
, p. 931 - 934 (2006)
A series of meso-tetraaryl porphyrins with fused phenanthrene rings have been synthesized from boron trifluoride-catalyzed Lindsey condensation of phenanthro[9,10-c]pyrrole with various para-substituted arylaldehydes at low temperature. Their structures w
