Solvent‐free Reactions for the Synthesis of Indolenine‐based Squaraines and Croconaines: Comparison of Thermal Heating, Mechanochemical Milling, and IR Irradiation

Zappimbulso, Nicola; Capozzi, Maria Annunziata M.; Porcheddu, Andrea; Farinola, Gianluca M.; Punzi, Angela

doi:10.1002/cssc.202002763

Cited by 19 publications

(11 citation statements)

References 33 publications

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“…Solvent-free protocols can be performed as well (Escobedo et al, 2016). Applications in food processing and organic synthesis, the latter providing some improvements over MW or mechanical activation, have been reported (Aboud et al, 2019;Zappimbulso et al, 2021).…”

Section: Infrared Heatingmentioning

confidence: 99%

Process intensification in continuous flow organic synthesis with enabling and hybrid technologies

et al. 2022

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Industrial organic synthesis is time and energy consuming, and generates substantial waste. Traditional conductive heating and mixing in batch reactors is no longer competitive with continuous-flow synthetic methods and enabling technologies that can strongly promote reaction kinetics. These advances lead to faster and simplified downstream processes with easier workup, purification and process scale-up. In the current Industry 4.0 revolution, new advances that are based on cyber-physical systems and artificial intelligence will be able to optimize and invigorate synthetic processes by connecting cascade reactors with continuous in-line monitoring and even predict solutions in case of unforeseen events. Alternative energy sources, such as dielectric and ohmic heating, ultrasound, hydrodynamic cavitation, reactive extruders and plasma have revolutionized standard procedures. So-called hybrid or hyphenated techniques, where the combination of two different energy sources often generates synergistic effects, are also worthy of mention. Herein, we report our consolidated experience of all of these alternative techniques.

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Section: Infrared Heatingmentioning

confidence: 99%

Process intensification in continuous flow organic synthesis with enabling and hybrid technologies

et al. 2022

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“…Non-conventional types of media, such as deep eutectic solvents, have been recently shown to be suitable for the synthesis of squaraine dyes [21]. Furthermore, solvent-free approaches to some squaraine dyes have been introduced [22]. These novel approaches might prove to be a viable complement to traditional synthetic routes to squaraines.…”

Section: Squaric Acid-based Synthesesmentioning

confidence: 99%

Squaraine-Based Optical Sensors: Designer Toolbox for Exploring Ionic and Molecular Recognitions

Dzyuba

2021

Chemosensors

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Small molecule-based chromogenic and fluorogenic probes play an indispensable role in many sensing applications. Ideal optical chemosensors should provide selectivity and sensitivity towards a variety of analytes. Synthetic accessibility and attractive photophysical properties have made squaraine dyes an enticing platform for the development of chemosensors. This review highlights the versatility of modular assemblies of squaraine-based chemosensors and chemodosimeters that take advantage of the availability of various structurally and functionally diverse recognition motifs, as well as utilizing additional recognition capabilities due to the unique structural features of the squaraine ring.

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“…For this reason, it is important to investigate the reaction process in detail and to reveal the reaction mechanism. 14 − 16 …”

Section: Introductionmentioning

confidence: 99%

Exploring the In Situ Formation Mechanism of Polymeric Aluminum Chloride–Silica Gel Composites under Mechanical Grinding Conditions: As a High-Performance Nanocatalyst for the Synthesis of Xanthene and Pyrimidinone Compounds

et al. 2022

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The use of mechanical ball milling to facilitate the synthesis of organic compounds has attracted intense interest from organic chemists. Herein, we report a new process for the preparation of xanthene and pyrimidinone compounds by a one-pot method using polymeric aluminum chloride (PAC), silica gel, and reaction raw materials under mechanical grinding conditions. During the grinding process, polymeric aluminum chloride and silica gel were reconstituted in situ to obtain a new composite catalyst (PAC–silica gel). This catalyst has good stability (six cycles) and wide applicability (22 substrates). The Al–O–Si active center formed by in situ grinding recombination was revealed to be the key to the effective catalytic performance of the PAC–silica gel composites by the comprehensive analysis of the catalytic materials before and after use. In addition, the mechanism of action of the catalyst was verified using density functional theory, and the synthetic pathway of the xanthene compound was reasonably speculated with the experimental data. Mechanical ball milling serves two purposes in this process: not only to induce the self-assembly of silica and PAC into new composites but also to act as a driving force for the catalytic reaction to take place. From a practical point of view, this “one-pot” catalytic method eliminates the need for a complex preparation process for catalytic materials. This is a successful example of the application of mechanochemistry in materials and organic synthesis, offering unlimited possibilities for the application of inorganic polymer materials in green synthesis and catalysis promoted by mechanochemistry.

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Solvent‐free Reactions for the Synthesis of Indolenine‐based Squaraines and Croconaines: Comparison of Thermal Heating, Mechanochemical Milling, and IR Irradiation

Cited by 19 publications

References 33 publications

Process intensification in continuous flow organic synthesis with enabling and hybrid technologies

Process intensification in continuous flow organic synthesis with enabling and hybrid technologies

Squaraine-Based Optical Sensors: Designer Toolbox for Exploring Ionic and Molecular Recognitions

Exploring the In Situ Formation Mechanism of Polymeric Aluminum Chloride–Silica Gel Composites under Mechanical Grinding Conditions: As a High-Performance Nanocatalyst for the Synthesis of Xanthene and Pyrimidinone Compounds

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