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The 160th Anniversary of the Schiff Base Discovery: Obtaining Functional...
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The 160th Anniversary of the Schiff Base Discovery: Obtaining Functional Molecules with Schiff Bases

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Inorganic Chemistry".

Deadline for manuscript submissions: closed (31 July 2024) | Viewed by 4840

Special Issue Editor

Prof. Dr. Takashiro Akitsu

E-Mail Website
Guest Editor
Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Tokyo 162-8601, Japan
Interests: inorganic chemistry; coordination chemistry; Schiff base; crystallography
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Schiff bases (imine or azomethine -N=CH-), which were first obtained by the German chemist H. Schiff in 1864, may be a part of a popular group of organic compounds prepared form primary amines and aldehyde or ketone. Many studies have been carried out on Schiff bases not only as organic compounds, but also as ligands for metal complexes. Schiff base ligands played an important role in the development of inorganic coordination chemistry and were an essential point in the development of bioinorganic chemistry and optical or magnetic materials in the solid state. These are most widely used as intermediates in organic synthesis, and applied for catalysts, pigments and dyes, polymer stabilizers, etc. As such, this Special Issue is aimed at a comprehensive, interdisciplinary review of Schiff base compounds, with an emphasis on the latest advances, including the basic (physical and chemical) properties of Schiff bases; the formation mechanism or principles in the synthesis of Schiff bases; reactions associated with Schiff bases; Schiff base ligands for metal complexes; analysis or classification of Schiff base compounds; medicinal or biological application of Schiff bases; and usage of Schiff bases in materials or engineering.

Prof. Dr. Takashiro Akitsu
Guest Editor

Manuscript Submission Information

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Keywords

  • azomethine
  • imine
  • synthesis
  • functions
  • Schiff base

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Published Papers (3 papers)

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Editorial

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3 pages, 208 KiB  
Editorial
Recent Advances in Chiral Schiff Base Compounds in 2023
by China Takeda, Daisuke Nakane and Takashiro Akitsu
Molecules 2023, 28(24), 7990; https://doi.org/10.3390/molecules28247990 - 7 Dec 2023
Cited by 1 | Viewed by 1533
Abstract
Schiff bases (imine or azomethine –N=CH–), which were first obtained by a German chemist, H [...] Full article
(This article belongs to the Special Issue The 160th Anniversary of the Schiff Base Discovery: Obtaining Functional Molecules with Schiff Bases)

Research

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18 pages, 3162 KiB  
Article
Isolated Dipolar ONN Schiff Base Regioisomers: Synthesis, Characterization and Crystallographic Study
by Pablo Castro-Tamay, David Villaman, Jean-René Hamon and Néstor Novoa
Molecules 2024, 29(24), 5863; https://doi.org/10.3390/molecules29245863 - 12 Dec 2024
Viewed by 501
Abstract
Organic compounds with 1,3-diketone or 3-amino enone functional groups are extremely important as they can be converted into a plethora of carbo- or heterocyclic derivatives or can be used as ligands in the formation of metal complexes. Here, we have achieved the preparation [...] Read more.
Organic compounds with 1,3-diketone or 3-amino enone functional groups are extremely important as they can be converted into a plethora of carbo- or heterocyclic derivatives or can be used as ligands in the formation of metal complexes. Here, we have achieved the preparation of a series of non-symmetrical β-ketoenamines (O,N,N proligand) of the type (4-MeOC6H4)C(=O)CH=C(R)NH(Q) obtained through the Schiff base condensation of 1,3-diketones (1-anisoylacetone, 1-anisyl-3-(4-cyanophenyl)-1,3-propanedione, and 1-anisyl-3-(4,4,4-trifluorotolyl)-1,3-propanedione) functionalized with electron donor and electron-withdrawing substituents and 8-aminoquinoline (R = CH3, 4-C6H4CN, 4-C6H4CF3; Q = C9H7N). Schiff base ketoimines with a pendant quinolyl moiety were isolated as single regioisomers in yields of 22–56% and characterized with FT-IR, 1H NMR, and UV-visible spectroscopy, as well as single-crystal X-ray crystallography, which allowed for the elucidation of the nature of the isolated regioisomers. The regioselectivity of the condensation of electronically unsymmetrical 1,3-diaryl-1,3-diketones with 8-aminoquinoline was studied by 1H NMR, providing regioisomer ratios of ~3:1 and ~2:1 in the case of CN and CF3 substituents, respectively. The electronic effects correlate well with the difference between the Hammett σ+ coefficients of the two para substituents on the aryl rings. Full article
(This article belongs to the Special Issue The 160th Anniversary of the Schiff Base Discovery: Obtaining Functional Molecules with Schiff Bases)
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Review

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25 pages, 7644 KiB  
Review
Towards Industrially Important Applications of Enhanced Organic Reactions by Microfluidic Systems
by Ayesha Zafar, China Takeda, Asif Manzoor, Daiki Tanaka, Masashi Kobayashi, Yoshitora Wadayama, Daisuke Nakane, Adnan Majeed, Muhammad Adnan Iqbal and Takashiro Akitsu
Molecules 2024, 29(2), 398; https://doi.org/10.3390/molecules29020398 - 13 Jan 2024
Cited by 9 | Viewed by 2274
Abstract
This review presents a comprehensive evaluation for the manufacture of organic molecules via efficient microfluidic synthesis. Microfluidic systems provide considerably higher control over the growth, nucleation, and reaction conditions compared with traditional large-scale synthetic methods. Microfluidic synthesis has become a crucial technique for [...] Read more.
This review presents a comprehensive evaluation for the manufacture of organic molecules via efficient microfluidic synthesis. Microfluidic systems provide considerably higher control over the growth, nucleation, and reaction conditions compared with traditional large-scale synthetic methods. Microfluidic synthesis has become a crucial technique for the quick, affordable, and efficient manufacture of organic and organometallic compounds with complicated characteristics and functions. Therefore, a unique, straightforward flow synthetic methodology can be developed to conduct organic syntheses and improve their efficiency. Full article
(This article belongs to the Special Issue The 160th Anniversary of the Schiff Base Discovery: Obtaining Functional Molecules with Schiff Bases)
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