Co(<scp>ii</scp>), Ni(<scp>ii</scp>), Cu(<scp>ii</scp>) and Zn(<scp>ii</scp>) complexes of tetraphenylazadipyrromethene

Palma, Aniello; Gallagher, John F.; Müller‐Bunz, Helge; Wolowska, Joanna; McInnes, Eric J. L.; O’Shea, Donal F.

doi:10.1039/b811764k

Cited by 62 publications

(91 citation statements)

References 35 publications

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“…The BF 2 + chelation was carried out according to the literature procedures in moderate yields (Scheme 2) [2,5]. For the zinc(II) chelation, the reaction was changed from a reaction using Zn(OAc) 2 to a 2-step, one pot reaction with sodium hydride in tetrahydrofuran, followed by the addition of zinc(II) chloride.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

Etheridge¹,

Fernando²,

Pejić³

et al. 2016

Beilstein J. Org. Chem.

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SummaryHomoleptic zinc(II) complexes of di(phenylacetylene)azadipyrromethene (e.g., Zn(WS3)2) are potential non-fullerene electron acceptors for organic photovoltaics. To tune their properties, fluorination of Zn(WS3)2 at various positions was investigated. Three fluorinated azadipyrromethene-based ligands were synthesized with fluorine at the para-position of the proximal and distal phenyl groups, and at the pyrrolic phenylacetylene moieties. Additionally, a CF3 moiety was added to the pyrrolic phenyl positions to study the effects of a stronger electron withdrawing unit at that position. The four ligands were chelated with zinc(II) and BF2 + and the optical and electrochemical properties were studied. Fluorination had little effect on the optical properties of both the zinc(II) and BF2 + complexes, with λmax in solution around 755 nm and 785 nm, and high molar absorptivities of 100 × 103 M−1cm−1 and 50 × 103 M−1cm−1, respectively. Fluorination of Zn(WS3)2 raised the oxidation potentials by 0.04 V to 0.10 V, and the reduction potentials by 0.01 V to 0.10 V, depending on the position and type of substitution. The largest change was observed for fluorine substitution at the proximal phenyl groups and CF3 substitution at the pyrrolic phenylacetylene moieties. The later complexes are expected to be stronger electron acceptors than Zn(WS3)2, and may enable charge transfer from other conjugated polymer donors that have lower energy levels than poly(3-hexylthiophene) (P3HT).

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Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

Etheridge¹,

Fernando²,

Pejić³

et al. 2016

Beilstein J. Org. Chem.

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“…1 Specifically the homoleptic copper complex of 39 (M = Cu) was noted as having "excellent light fastness, being equal to Prussian-blue". More recently these complexes have been fully characterised 30 …”

Section: Scheme 13 Synthesis Of Bf2-azadipyrromethenementioning

confidence: 99%

Azadipyrromethenes: from traditional dye chemistry to leading edge applications

2016

Self Cite

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Azadipyrromethenes were first described over 70 years ago as blue pigments, but now are rapidly emerging as a compound class with highly desirable near infrared photophysical properties. Since the turn of the century several routes to azadipyrromethenes have been developed and numerous post-synthesis derivatizations have allowed for their exploitation in both biological and material sciences. The relative ease of access to specifically designed derivatives is now allowing their use in multiple technological formats from real-time fluorescence imaging, to solar energy materials, to optoelectronic devices and many more. In this review we have highlighted the synthetic component of this story as it is the ability to generate the designer azadipyrromethene that opens the door to exciting applications.

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“…The apparent Q*'' and Q*' intensities should be the statistical result of coupled surface complexes with various structures. The relatively large energy gap between Q*'' and Q*' is comparable to those of some typical intramolecular exciton couplings in coordination compounds such as [M(dipyrrinato) 3 ] (M= Co, Rh, Ga, or In) and [M(tp-azadp) 2 ] (M= Co, Ni, Zn or Cu; tp-azadp = tetraphenylazadipyrromethene) [33][34][35][36][37] and indicates strong exciton coupling. From the crystal structure of ZnS, the shortest distance between two neighboring Zn atoms in the ZnS NC surface is 0.38 nm.…”

Section: Resultsmentioning

confidence: 92%

“…Exciton coupling related to electronic overlap was found in Cu II complexes. [37] The optical and electronic structure of the ZnQ 2 complex as an electroluminescent material in organic light-emitting diodes, which has been calculated and measured, [38][39][40][41] which can be feasibly compared with the above assignment of the excitation states of the surface complex in ZnS-Q NCs. It is generally accepted that the strongest optical absorption of ZnQ 2 at about 400 nm is the p!p* transition localized on the Q ligands and that the Zn atom contributes very little to the electron-density distribution of the frontier orbitals.…”

Section: Resultsmentioning

confidence: 99%

Exciton Coupling of Surface Complexes on a Nanocrystal Surface

Wang

et al. 2014

ChemPhysChem

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Exciton coupling may arise when chromophores are brought into close spatial proximity. Herein the intra-nanocrystal exciton coupling of the surface complexes formed by coordination of 8-hydroxyquinoline to ZnS nanocrystals (NCs) is reported. It is studied by absorption, photoluminescence (PL), PL excitation (PLE), and PL lifetime measurements. The exciton coupling of the surface complexes tunes the PL color and broadens the absorption and PLE windows of the NCs, and thus is a potential strategy for improving the light-harvesting efficiency of NC solar cells and photocatalysts.

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Co(ii), Ni(ii), Cu(ii) and Zn(ii) complexes of tetraphenylazadipyrromethene

Abstract: The synthesis, crystallographic and spectroscopic properties of four divalent isomorphous metal complexes of tetraphenylazadipyrromethene are described.

Cited by 62 publications

References 35 publications

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

Azadipyrromethenes: from traditional dye chemistry to leading edge applications

Exciton Coupling of Surface Complexes on a Nanocrystal Surface

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