Porphycene with eight methoxy substituents at its β-positions was synthesized for the first time in three steps from 3,4-dimethoxypyrrole. The presence of methoxy groups increases its hydrophilicity as evident from their increased solubility in methanol. Among its metallo-derivatives, the Pd(II)-complex displays efficient singlet oxygen quantum yield (73%) and hence can be a potentially good photosensitizer for photo-oxidation, DNA cleavage, and photodynamic therapy (PDT).
A series of porphyrins and their corresponding Zn(II)-derivatives possessing both electron donating and electron withdrawing substituents at their periphery, have been investigated for the detection of nitrated explosives, which includes nitroaromatics, plastic explosive taggant (DMNB) and explosive nitramines (RDX and HMX), using a fluorescence turn-off mechanism. Among them, b-octamethoxyporphyrin displays the maximum response towards TNT with a K SV of 324 M 21 .
A novel electron deficient β-octakis(methylthio)porphycene, along with its Zn(ii) and Ni(ii) derivatives, was synthesized for the first time. The macrocyclic structure exhibits core ruffling with a largely red shifted absorption band (∼750 nm) and also a large enhancement in the third order nonlinear optical response.
We report the regiospecific synthesis of the first chloro-substituted porphycenes as two positional isomers of β-tetrachlorotetramethoxyporphycene. The positional effect of the substituents on these isomers could be clearly distinguished in their structure and photophysical properties.
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