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Methyl Ester Functionalized Phenalenyl Arene- and Bipyridine-Ruthenium-Based Complexes for Electroactive Langmuir-Blodgett Films.
Inorg Chem 2019; 58(13):8408-8418IC

Abstract

We report the synthesis of a new phenalenyl ligand, functionalized with a methyl ester electron withdrawing group, named 9-hydroxy-1-oxo-1 H-phenalen-5-methyl carboxylate (L), and the generated complexes [Ru(bpy)2L]PF6 and [(η6-C6H6)Ru(L)Cl]. Compounds were characterized by spectroscopic and X-ray diffraction methods, and their electrochemical behavior was investigated via cyclic voltammetry and UV-vis spectroelectrochemistry. The one-electron oxidized compounds have an unpaired electron located in the phenalenyl ring, as supported by theoretical calculations (DFT) and EPR results. Langmuir-Blodgett (LB) films deposited by [Ru(bpy)2L]2+/3+ species mixed with stearic acid are electroactive, showing a quasi-reversible wave with E1/2Film1 = 0.74 V and E1/2Film2 = 0.81, which are promising systems that allow access to immobilized open-shell species in the film.

Authors+Show Affiliations

Departamento de Química , Universidade Federal do Paraná , 81530-900 , Curitiba - Paraná , Brazil.Departamento Acadêmico de Química e Biologia , Universidade Tecnológica Federal do Paraná , 81280-340 , Curitiba - Paraná , Brazil.Departamento de Química , Universidade Federal do Paraná , 81530-900 , Curitiba - Paraná , Brazil.Departamento de Química , Universidade Federal do Paraná , 81530-900 , Curitiba - Paraná , Brazil.School of Chemistry , University of East Anglia , Norwich NR4 7TJ , United Kingdom.Departamento de Química , Universidade Federal do Paraná , 81530-900 , Curitiba - Paraná , Brazil.Departamento de Química , Universidade Federal do Paraná , 81530-900 , Curitiba - Paraná , Brazil.Departamento de Química , Universidade Federal do Paraná , 81530-900 , Curitiba - Paraná , Brazil.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31247853

Citation

Wahl, Isis Mani, et al. "Methyl Ester Functionalized Phenalenyl Arene- and Bipyridine-Ruthenium-Based Complexes for Electroactive Langmuir-Blodgett Films." Inorganic Chemistry, vol. 58, no. 13, 2019, pp. 8408-8418.
Wahl IM, Westphal E, Leyser da Costa Gouveia T, et al. Methyl Ester Functionalized Phenalenyl Arene- and Bipyridine-Ruthenium-Based Complexes for Electroactive Langmuir-Blodgett Films. Inorg Chem. 2019;58(13):8408-8418.
Wahl, I. M., Westphal, E., Leyser da Costa Gouveia, T., Santana, F. S., Hughes, D. L., Ribeiro, R. R., ... Winnischofer, H. (2019). Methyl Ester Functionalized Phenalenyl Arene- and Bipyridine-Ruthenium-Based Complexes for Electroactive Langmuir-Blodgett Films. Inorganic Chemistry, 58(13), pp. 8408-8418. doi:10.1021/acs.inorgchem.9b00530.
Wahl IM, et al. Methyl Ester Functionalized Phenalenyl Arene- and Bipyridine-Ruthenium-Based Complexes for Electroactive Langmuir-Blodgett Films. Inorg Chem. 2019 Jul 1;58(13):8408-8418. PubMed PMID: 31247853.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Methyl Ester Functionalized Phenalenyl Arene- and Bipyridine-Ruthenium-Based Complexes for Electroactive Langmuir-Blodgett Films. AU - Wahl,Isis Mani, AU - Westphal,Eduard, AU - Leyser da Costa Gouveia,Tiago, AU - Santana,Francielli Sousa, AU - Hughes,David L, AU - Ribeiro,Ronny R, AU - Piccoli,Leonardo Henrique Ribeiro, AU - Winnischofer,Herbert, Y1 - 2019/06/19/ PY - 2019/6/30/pubmed PY - 2019/6/30/medline PY - 2019/6/29/entrez SP - 8408 EP - 8418 JF - Inorganic chemistry JO - Inorg Chem VL - 58 IS - 13 N2 - We report the synthesis of a new phenalenyl ligand, functionalized with a methyl ester electron withdrawing group, named 9-hydroxy-1-oxo-1 H-phenalen-5-methyl carboxylate (L), and the generated complexes [Ru(bpy)2L]PF6 and [(η6-C6H6)Ru(L)Cl]. Compounds were characterized by spectroscopic and X-ray diffraction methods, and their electrochemical behavior was investigated via cyclic voltammetry and UV-vis spectroelectrochemistry. The one-electron oxidized compounds have an unpaired electron located in the phenalenyl ring, as supported by theoretical calculations (DFT) and EPR results. Langmuir-Blodgett (LB) films deposited by [Ru(bpy)2L]2+/3+ species mixed with stearic acid are electroactive, showing a quasi-reversible wave with E1/2Film1 = 0.74 V and E1/2Film2 = 0.81, which are promising systems that allow access to immobilized open-shell species in the film. SN - 1520-510X UR - https://www.unboundmedicine.com/medline/citation/31247853/Methyl_Ester_Functionalized_Phenalenyl_Arene-_and_Bipyridine-Ruthenium-Based_Complexes_for_Electroactive_Langmuir-Blodgett_Films L2 - https://dx.doi.org/10.1021/acs.inorgchem.9b00530 DB - PRIME DP - Unbound Medicine ER -