Gram‐Scale Synthesis of Nickel(II) Norcorrole: The Smallest Antiaromatic Porphyrinoid

Abstract

Small is beautiful: A ring-contracted sister of porphyrin, norcorrole, has been synthesized efficiently as a stable molecule by a nickel-templated strategy. The norcorrole complex is stable but exhibits a distinct antiaromatic character according to the Hückel rule. Oxidation of the norcorrole complex provides an aromatic oxacorrole complex.

A glassy carbon electrode modified with a nickel(II) norcorrole complex and carbon nanotubes for simultaneous or individual determination of ascorbic acid, dopamine, and uric acid

“…NiNC exhibits five absorption bands at 259, 290, 428, 474, and 514 nm, respectively. They are very similar to the reported [12,23]. The maximum absorption is at 428 nm.…”

“…Prior to use, it was purified by refluxing in concentrated nitric acid for 6 h, followed by centrifugation, resuspension and filtration and dried to evaporate the solvent. NiNC was synthesized as described in the literatures [12][13][14]. Uric acid (UA), ascorbic acid (AA) and dopamine (DA) were purchased from SigmaAldrich (http://www.sigmaaldrich.com).…”

“…Norcorrole, a ring-contracted porphyrinoid that lacks two of the meso-carbon atoms, was first synthesized [11]. The alternative approach allows us to efficiently prepare the stable diamagnetic nickel(II) norcorrole complex (NiNC) [12][13][14]. NiNC displays to be antiaromatic because of its highly planar structure and the presence of 16 π electrons along the conjugation circuit.…”

“…Also, there is no work about the electrocatalytic property of the complex. Here, nickel(II) norcorrole (NiNC), the smallest antiaromatic porphyrinoid [12], was used to construct the composite of NiNC with CNT. Different techniques were applied to characterize the hybrid.…”

Photophysical properties of tetraphenylporphyrinsubphthalocyanine conjugates

“…Although the bridging oxygen atom is sp 3 hybridized there appeared to be scope for an interaction between the ring moieties, since the lone pairs can interact significantly with the -system of the phenyl ring. For example, the recent spectroscopic characterization and theoretical analysis of a novel nickel 10-oxacorrole complex by Kobayashi and co-workers demonstrated that an sp 3 hybridized oxygen atom can form part of a cyclic -system with properties very similar to those of a conventional 18--electron heteroaromatic -system of a porphyrinoid ligand [19].…”