Extending a porphyrin chromophore via fusion with naphthalene

Abstract

An intramolecular oxidative aromatic coupling of meso-substituted porphyrins bearing electron-rich aromatics was the focus of investigation. The formation of C–C bond at [Formula: see text]-position for macrocycles bearing dimethoxynaphthalene moiety was achieved. It was established that Fe(ClO[Formula: see text]O induced only single cyclodehydrogenation whereas Fe(OTf)[Formula: see text] had the ability to remove four hydrogens and four electrons forming doubly-fused porphyrin. Both Fe(ClO[Formula: see text]O and Fe(OTf)[Formula: see text] were confirmed superior to FeCl[Formula: see text] as they ensured efficient oxidation process without concomitant chlorination of the products. We have proven that the trans-A[Formula: see text]B[Formula: see text]-porphyrin with two indole moieties do not form any stable products under such reaction conditions. The single fusion with dimethoxynaphthalene moiety has a comparable effect on absorption spectra [Formula: see text]. the Q-band of Ni-complexes is shifted to 650 nm. The Ni-porphyrin fused with two naphthalene units had bathochromically shifted Q-bands to 733 nm.

Molecular flattening effect to enhance the conductivity of fused porphyrin tape thin films

“…33,51,52 The fusion of aromatic rings on the porphyrin core was already observed in presence of iron oxidants, yet electron-donating groups on the phenyl rings are usually required. 20,21,53 However, so far the poor solubility of the oligomeric and polymeric products of the oCVD process hindered an unequivocal assignment and a proper characterization of the cyclization reaction.…”

Influence of Acid Catalyst on the Synthesis of trans‐Porphyrins and Crystal Structure of a 5‐(Pyren‐1‐yl)dipyrromethane

“…Notably, in both types of acidic conditions (Table 2), generally, the trans ‐ A 2 BC is formed in 2‐to‐3 fold higher yields when compared to other trans isomers ( A 2 B 2 or A 2 C 2 ). The selective synthesis of some trans ‐A 2 B 2 porphyrins has been reported in the literature [24,25] …”

“…The selective synthesis of some trans-A 2 B 2 porphyrins has been reported in the literature. [24,25] Push-pull porphyrins, trans-A 2 BC, find use in certain potential applications, [4][5][6][7][8] and the ester porphyrins, 1 a-5 a were de-esterified using reported procedures [18] followed by Zn(II) insertion to obtain Zn-1 c, Zn-3 c to Zn-5 c (Figure 1). These porphyrins were isolated in good to excellent yields (Figure 1).…”

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…Examples of naphthalene-fused porphyrins C30.3 and C30.4 – 5 obtained using intramolecular oxidative aromatic coupling were reported by Gryko et al (Chart ). Prasanthkumar, Giribabu and co-workers developed a related design based on a doubly fused anthracene linker C30.6 (Chart ).…”