Mono(arylhydrazino)acenaphthenones as a platform for the design of NIR chromophores based on Pd(ii)-BIAN complexes

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Mono(arylhydrazino)acenaphthenones as a platform for the design of NIR chromophores based on Pd(ii)-BIAN complexes. / Bakaev, I. V.; Romashev, N. F.; Komlyagina, V. I. et al.

In: New Journal of Chemistry, Vol. 47, No. 40, 21.09.2023, p. 18825-18834.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{26c214f5bcda475e85730014816520ce,

title = "Mono(arylhydrazino)acenaphthenones as a platform for the design of NIR chromophores based on Pd(ii)-BIAN complexes",

abstract = "A new synthetic procedure for mono(arylhydrazino)acenaphthenones Ph-mhan (1) and 2-tol-mhan (2), based on the reaction of acenaphthenequinone with an arylhydrazonium salt, has been developed. These compounds were used further to obtain a series of heteroleptic cationic palladium(ii) complexes containing bis(arylimino)acenaphthene (Ar-bian) and mono(arylhydrazino)acenaphthenone (Ar-mhan) ligands: [Pd(tmp-bian)(Ph-mhan)](CF3SO3)2 (3), [Pd(tmp-bian)(2-tol-mhan)](CF3SO3)2, (4), and [Pd(dpp-bian)(Ph-mhan)](CF3SO3)2 (5). The resulting compounds were characterized by X-ray diffraction analysis, 1H NMR, IR and UV spectroscopy, cyclic voltammetry, and quantum chemical calculations. All complexes show a reversible reduction at −0.31 to −0.41 V (vs. Ag/AgCl) localized on the Ar-bian ligand, followed by an irreversible reduction at −1.27 to −1.46 V (vs. Ag/AgCl) of the Ar-mhan moiety. Electronic absorption spectra of 3-5 reveal a characteristic band in the near-IR region (∼700 nm), corresponding to the intramolecular ligand-to-ligand charge transfer (LL′CT) from Ar-mhan (π-donor) to Ar-bian (π-acceptor).",

author = "Bakaev, {I. V.} and Romashev, {N. F.} and Komlyagina, {V. I.} and Samsonenko, {D. G.} and Gushchin, {A. L.}",

note = "The authors thank the Ministry of Science and Higher Education of the Russian Federation and the Centre of Collective Usage of NIIC SB RAS. They also thank the XRD Facility of NIIC SB RAS for the SCXRD data collection. Публикация для корректировки.",

year = "2023",

month = sep,

day = "21",

doi = "10.1039/d3nj03832g",

language = "English",

volume = "47",

pages = "18825--18834",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "ROYAL SOC CHEMISTRY",

number = "40",

}

RIS

TY - JOUR

T1 - Mono(arylhydrazino)acenaphthenones as a platform for the design of NIR chromophores based on Pd(ii)-BIAN complexes

AU - Bakaev, I. V.

AU - Romashev, N. F.

AU - Komlyagina, V. I.

AU - Samsonenko, D. G.

AU - Gushchin, A. L.

N1 - The authors thank the Ministry of Science and Higher Education of the Russian Federation and the Centre of Collective Usage of NIIC SB RAS. They also thank the XRD Facility of NIIC SB RAS for the SCXRD data collection. Публикация для корректировки.

PY - 2023/9/21

Y1 - 2023/9/21

N2 - A new synthetic procedure for mono(arylhydrazino)acenaphthenones Ph-mhan (1) and 2-tol-mhan (2), based on the reaction of acenaphthenequinone with an arylhydrazonium salt, has been developed. These compounds were used further to obtain a series of heteroleptic cationic palladium(ii) complexes containing bis(arylimino)acenaphthene (Ar-bian) and mono(arylhydrazino)acenaphthenone (Ar-mhan) ligands: [Pd(tmp-bian)(Ph-mhan)](CF3SO3)2 (3), [Pd(tmp-bian)(2-tol-mhan)](CF3SO3)2, (4), and [Pd(dpp-bian)(Ph-mhan)](CF3SO3)2 (5). The resulting compounds were characterized by X-ray diffraction analysis, 1H NMR, IR and UV spectroscopy, cyclic voltammetry, and quantum chemical calculations. All complexes show a reversible reduction at −0.31 to −0.41 V (vs. Ag/AgCl) localized on the Ar-bian ligand, followed by an irreversible reduction at −1.27 to −1.46 V (vs. Ag/AgCl) of the Ar-mhan moiety. Electronic absorption spectra of 3-5 reveal a characteristic band in the near-IR region (∼700 nm), corresponding to the intramolecular ligand-to-ligand charge transfer (LL′CT) from Ar-mhan (π-donor) to Ar-bian (π-acceptor).

AB - A new synthetic procedure for mono(arylhydrazino)acenaphthenones Ph-mhan (1) and 2-tol-mhan (2), based on the reaction of acenaphthenequinone with an arylhydrazonium salt, has been developed. These compounds were used further to obtain a series of heteroleptic cationic palladium(ii) complexes containing bis(arylimino)acenaphthene (Ar-bian) and mono(arylhydrazino)acenaphthenone (Ar-mhan) ligands: [Pd(tmp-bian)(Ph-mhan)](CF3SO3)2 (3), [Pd(tmp-bian)(2-tol-mhan)](CF3SO3)2, (4), and [Pd(dpp-bian)(Ph-mhan)](CF3SO3)2 (5). The resulting compounds were characterized by X-ray diffraction analysis, 1H NMR, IR and UV spectroscopy, cyclic voltammetry, and quantum chemical calculations. All complexes show a reversible reduction at −0.31 to −0.41 V (vs. Ag/AgCl) localized on the Ar-bian ligand, followed by an irreversible reduction at −1.27 to −1.46 V (vs. Ag/AgCl) of the Ar-mhan moiety. Electronic absorption spectra of 3-5 reveal a characteristic band in the near-IR region (∼700 nm), corresponding to the intramolecular ligand-to-ligand charge transfer (LL′CT) from Ar-mhan (π-donor) to Ar-bian (π-acceptor).

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85174385098&origin=inward&txGid=d1ef7fcd65636e4a408e020d7631e2d0

UR - https://www.mendeley.com/catalogue/d4ec19d2-7ef2-39d6-a351-13e04a45c16a/

U2 - 10.1039/d3nj03832g

DO - 10.1039/d3nj03832g

M3 - Article

VL - 47

SP - 18825

EP - 18834

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 40

ER -

ID: 59554358