Biomedical

Selective Schiff Base Formation of Group 9 Organometallic Complexes with Functionalized Spirobifluorene Ligands

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Krystal M. Cid-Seara,

Krystal M. Cid-Seara

Departamento de Química Inorgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, Spain


Raquel Pereira-Cameselle,

Raquel Pereira-Cameselle

Departamento de Química Orgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, Spain


Sandra Bolaño,

Sandra Bolaño

Departamento de Química Inorgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, Spain


Maria Talavera

Maria Talavera

Departamento de Química Inorgánica, Universidade de Vigo, Campus Universitario, 36310 Vigo, Spain


  Peer Reviewed

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© attribution CC-BY

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Added on

2024-12-01

Doi: http://dx.doi.org/10.3390/molecules28207155
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Abstract

Organic amines are important compounds present in a wide variety of products, which makes the development of new systems for their detection an interesting field of study. New organometallic complexes of group 9 [MCp*X(2′-R-2-py-SBF)] (M = Ir, Rh; R = H, X = Cl (6), R = H, X = OAc (7), R = CHO, X = Cl (8)), and [IrCp*Cl(2′, 7-diCHO-2-py-SBF)] (9) (Cp* pentamethylcyclopentadienyl, SBF = 9,9’-spirobifluorene) bearing bidentate C–N ligands based on 9,9′-spirobifluorene were obtained and characterized by NMR spectroscopy, mass spectrometry, IR spectroscopy, and X-ray diffraction analysis when possible. The formation of a Schiff base to give complexes with the formula [MCp*Cl(2′-CH=NR-2-py-SBF)] (M = Ir, Rh; R = alkyl or aryl (10–12)), through condensation of an amine, and the aldehyde group present in these new complexes was studied leading to a selective reactivity depending on the nature of the amine and the metal center. While the iridium complexes only react with aromatic amines, the rhodium derivative requires heat for those but can react at room temperature with aliphatic amines.

Key Questions

Amine Detection

How can organometallic complexes detect amines? What are new methods for sensing amines in products? Can iridium compounds detect amines through luminescence?

Organometallic Chemistry

What are cyclometallated complexes with bidentate C-N ligands? How do iridium and rhodium complexes differ in reactivity? What is the structure of pentamethylcyclopentadienyl metal complexes?

Spirobifluorene Compounds

What are the properties of 9,9'-spirobifluorene-based ligands? How can spirobifluorene be functionalized for various applications? What are the uses of spirobifluorene in materials science?

Schiff Base Formation

How do metal complexes form Schiff bases with amines? What factors affect Schiff base formation in organometallic compounds? Can Schiff base reactions be used for amine detection?

Related Subjects
Anatomy
Biochemistry
Epidemiology
Genetics
Neuroscience
Psychology
Oncology
Medicine
Musculoskeletal science
Pediatrics
Pathology
Pharmacology
Physiology
Psychiatry
Primary care
Women and reproductive health
copyright icon

© attribution CC-BY

  • 0

rating
145 Views

Added on

2024-12-01

Doi: http://dx.doi.org/10.3390/molecules28207155
Related Subjects
Anatomy
Biochemistry
Epidemiology
Genetics
Neuroscience
Psychology
Oncology
Medicine
Musculoskeletal science
Pediatrics
Pathology
Pharmacology
Physiology
Psychiatry
Primary care
Women and reproductive health