A Simple and Efficient Mechanochemical Route for the Synthesis of Salophen Ligands and of the Corresponding Zn, Ni, and Pd Complexes

Leoni, Luca; Carletta, Andrea; Fusaro, Luca; Dubois, Jean; Tumanov, Nikolay; Aprile, Carmela; Wouters, Jan; Cort, Antonella Dalla

doi:10.3390/molecules24122314

Cited by 19 publications

(21 citation statements)

References 39 publications

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“…52 Alternatively, these species can be produced mechanochemically via neat or LAG conditions. 1,15,47,53 In a typical reaction, 5-bromosalicylaldehyde and a diamine (ethylenediamine, and 1, 2-phenylenediamine for salen and salophen ligands, respectively) were ground together in a 15 ml milling jar with a 8 mm diameter ball (both stainless steel) -see Fig. 3a).…”

Section: Resultsmentioning

confidence: 99%

“…46 Therefore, the need for solvent removal -which generally is an energy-intensive processremained inevitable. Later, Cort and co-workers 47 reported the LAG mechanosynthesis of a series of salophen transition metals complexes (i.e., M= Zn, Ni, Pd) -See Figure 1c. This method proceeded with yields ranging from 60 to 68% for the complexes reported.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Multi-gram Mechanosynthesis of Salophen-Complex: A Comparative Analysis

Garcı́a¹,

Ong²,

Singh³

et al. 2020

Preprint

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Mechanochemistry is a powerful alternative to traditional solvent-based synthesis as it is environmentally benign, allows for higher yields in shorter reaction times, while minimizing the use of solvents. Although mechanochemical routes are becoming increasingly mainstream in synthetic laboratories, up-scales examples for main group complexes are still rare. Here, motivated by the practical implementation of mechanosynthesis, we demonstrated the synthesis of salen and salophen complexes. The herein reported synthesis displays low E-factor and process mass intensity compared to conventional solution methods. In addition, analyses evaluating environmental parameters, energy consumption and production costs have been performed, showing the multiple advantages mechanochemistry has over convetional solution-based synthesis<br>

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Multi-gram Mechanosynthesis of Salophen-Complex: A Comparative Analysis

Garcı́a¹,

Ong²,

Singh³

et al. 2020

Preprint

View full text Add to dashboard Cite

show abstract

“…Among reports on synthesis of SB worth mentioning are the methods performed in ionic liquids [33], techniques with the use of ordered mesoporous materials [34], solvent free synthesis reaction performed under infrared [35], ultrasound [36] and microwave irradiation [37]. Direct synthesis mechanochemical methods are also applied to perform solid-solid synthesis [38][39][40] confirming the high reactivity of this group of compounds.…”

Section: Synthesis Methods Of Schiff Base Ligands and Their Complexesmentioning

confidence: 99%

Homo- and Hetero-Oligonuclear Complexes of Platinum Group Metals (PGM) Coordinated by Imine Schiff Base Ligands

Mirosław

2020

IJMS

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Chemistry of Schiff base (SB) ligands began in 1864 due to the discovery made by Hugo Schiff (Schiff, H., Justus Liebigs Ann. der Chemie 1864, 131 (1), 118–119). However, there is still a vivid interest in coordination compounds based on imine ligands. The aim of this paper is to review the most recent concepts on construction of homo- and hetero-oligonuclear Schiff base coordination compounds narrowed down to the less frequently considered complexes of platinum group metals (PGM). The combination of SB and PGM in oligonuclear entities has several advantages over mononuclear or polynuclear species. Such complexes usually exhibit better electroluminescent, magnetic and/or catalytic properties than mononuclear ones due to intermetallic interactions and frequently have better solubility than polymers. Various construction strategies of oligodentate imine ligands for coordination of PGM are surveyed including simple imine ligands, non-innocent 1,2-diimines, chelating imine systems with additional N/O/S atoms, classic N2O2-compartmental Schiff bases and their modifications resulting in acyclic fused ligands, macrocycles such as calixsalens, metallohelical structures, nano-sized molecular wheels and hybrid materials incorporating mesoionic species. Co-crystallization and formation of metallophilic interactions to extend the mononuclear entities up to oligonuclear coordination species are also discussed.

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“…Moreover, the same group has also reported the synthesis of salen and salophen complexes (nickel and zinc, respectively) using TSE methodologies both at medium scales (i.e., below 20 g); see Figure 1b,c (middle and top, respectively). In addition, Cort and co-workers 48 reported the LAG mechanosynthesis of a series of salophen transition metals complexes (i.e., M = Zn, Ni, Pd); see Figure 1c. This method proceeded with yields ranging from 60 to 68% for the complexes reported.…”

Section: ■ Introductionmentioning

confidence: 99%

Multigram Mechanochemical synthesis of a Salophen Complex: A Comparative Analysis

Singh

Chamberlain-Clay

Ong

et al. 2021

ACS Sustainable Chem. Eng.

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Mechanosynthesis is a powerful alternative to traditional solvent-based synthesis as it allows for higher yields in shorter reaction times, while minimizing the use of solvents. Although mechanochemical routes are becoming increasingly mainstream in synthetic laboratories, up-scaled examples for main group complexes are still rare. Here, motivated by the practical implementation of mechanosynthesis, we demonstrated the synthesis of salen and salophen complexes. The herein reported synthesis displays low E-factor and process mass intensity compared to conventional solution methods. In addition, analyses evaluating environmental parameters, energy consumption, and production cost have been performed, showing the multiple advantages mechanochemistry has over conventional solution-based synthesis.

show abstract

A Simple and Efficient Mechanochemical Route for the Synthesis of Salophen Ligands and of the Corresponding Zn, Ni, and Pd Complexes

Cited by 19 publications

References 39 publications

Multi-gram Mechanosynthesis of Salophen-Complex: A Comparative Analysis

Multi-gram Mechanosynthesis of Salophen-Complex: A Comparative Analysis

Homo- and Hetero-Oligonuclear Complexes of Platinum Group Metals (PGM) Coordinated by Imine Schiff Base Ligands

Multigram Mechanochemical synthesis of a Salophen Complex: A Comparative Analysis

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