Electrophilic Activation of Aldehydes “On Water”: A Facile Route to Dipyrromethanes

Zoli, Luca; Cozzi, Pier Giorgio

doi:10.1002/cssc.200900023

Cited by 17 publications

(5 citation statements)

References 47 publications

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“…Porphyrin 1 was prepared according to previously reported methods developed by Lindsey for the synthesis of trans -A2B2 type porphyrins involving BF 3 –ethanol cocatalysis . The [2 + 2] condensation of 5-mesityldipyromethane − (1 equiv) and culminaldehyde (1 equiv) in CHCl 3 containing 0.75% ethanol in the presence of BF 3 ·Et 2 O at room temperature (RT) for 2 h, followed by irreversible oxidation of the porphyrinogene intermediate with DDQ for an additional 1 h, afforded porphyrin 1 in 20% yield (DDQ = 2,3-dichloro-5,6-dicyano-1,4-benzoquinone). Further synthesis and characterization details are provided in the Supporting Information.…”

Section: Introductionsupporting

confidence: 80%

Interplay between π-Conjugation and Exchange Magnetism in One-Dimensional Porphyrinoid Polymers

et al. 2022

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The synthesis of novel polymeric materials with porphyrinoid compounds as key components of the repeating units attracts widespread interest from several scientific fields in view of their extraordinary variety of functional properties with potential applications in a wide range of highly significant technologies. The vast majority of such polymers present a closed-shell ground state, and, only recently, as the result of improved synthetic strategies, the engineering of open-shell porphyrinoid polymers with spin delocalization along the conjugation length has been achieved. Here, we present a combined strategy toward the fabrication of one-dimensional porphyrinoid-based polymers homocoupled via surface-catalyzed [3 + 3] cycloaromatization of isopropyl substituents on Au(111). Scanning tunneling microscopy and noncontact atomic force microscopy describe the thermal-activated intra- and intermolecular oxidative ring closure reactions as well as the controlled tip-induced hydrogen dissociation from the porphyrinoid units. In addition, scanning tunneling spectroscopy measurements, complemented by computational investigations, reveal the open-shell character, that is, the antiferromagnetic singlet ground state (S = 0) of the formed polymers, characterized by singlet–triplet inelastic excitations observed between spins of adjacent porphyrinoid units. Our approach sheds light on the crucial relevance of the π-conjugation in the correlations between spins, while expanding the on-surface synthesis toolbox and opening avenues toward the synthesis of innovative functional nanomaterials with prospects in carbon-based spintronics.

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Section: Introductionsupporting

confidence: 80%

Interplay between π-Conjugation and Exchange Magnetism in One-Dimensional Porphyrinoid Polymers

et al. 2022

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“…1 Precursor 1,3,5,7tetramethyl-8-phenyl-dipyrromethane was prepared using the procedure reported by Zoli and Cozzi. 2 Compound 3b 3 and 3d 4 were prepared according to literature procedures. Purification by flash column chromatography (7:3 cyclohexane:AcOEt) afforded the title compound 4h (94 % yield, 41 mg) as a colourless oil.…”

Section: Methodsmentioning

confidence: 99%

Photocatalytic ATRA reaction promoted by iodo-Bodipy and sodium ascorbate

et al. 2017

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“…Synthesis of o-I-BDP. Dipyrromethane was synthesized according to a modified literature procedure [14]. Deionized water (17 mL) was degassed in a Schlenk tube and 2-iodobenzaldehyde (0.42 mmol, 97 mg, 1 eq.)…”

Section: Synthesis Of Compoundsmentioning

confidence: 99%

“…The preparation of o-I-BDP was carried out with a slight modification of a synthetic procedure previously reported by one of us [14]. The synthesis takes advantage of the standard approach employed for BODIPY dyes.…”

Section: Synthesismentioning

confidence: 99%

Effect of the iodine atom position on the phosphorescence of BODIPY derivatives: a combined computational and experimental study

Bassan

Dai

Fazzi

et al. 2022

Photochem Photobiol Sci

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A new BODIPY derivative (o-I-BDP) containing an iodine atom in the ortho position of the meso-linked phenyl group was prepared. Photophysical and electrochemical properties of the molecule were compared to previously reported iodo BODIPY derivatives, as well as to the non-iodinated analog. While in the case of derivatives featuring iodine substituents in the BODIPY core, efficient population of the triplet state is accompanied by a substantial positive shift of the reduction potential compared to pristine BODIPY, o-I-BDP displays phosphorescence and simultaneously maintains the electrochemical properties of unsubstituted BODIPYs. A theoretical investigation was settled to analyze results and rationalize the influence of iodine position on electronic and photophysical properties, with the purpose of preparing a fully organic phosphorescent BODIPY derivative. TD-DFT and spin-orbit coupling calculations shed light on the subtle effects played by the introduction of iodine atom in different positions of BODIPY.

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Electrophilic Activation of Aldehydes “On Water”: A Facile Route to Dipyrromethanes

Cited by 17 publications

References 47 publications

Interplay between π-Conjugation and Exchange Magnetism in One-Dimensional Porphyrinoid Polymers

Interplay between π-Conjugation and Exchange Magnetism in One-Dimensional Porphyrinoid Polymers

Photocatalytic ATRA reaction promoted by iodo-Bodipy and sodium ascorbate

Effect of the iodine atom position on the phosphorescence of BODIPY derivatives: a combined computational and experimental study

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