Introducing 3D conjugated acceptors with intense red absorption: homoleptic metal(ii) complexes of di(phenylacetylene) azadipyrromethene

Senevirathna, Wasana; Sauvé, Geneviève

doi:10.1039/c3tc31377h

Cited by 39 publications

(61 citation statements)

References 61 publications

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“…Complex Zn(WS3) 2 is similar to our previously published Zn(WS1) 2 , [ 13 ] but without the t -butyl groups on the phenylethynyl conjugated arms. The synthesis and purifi cation of this complex are given in the Supporting Information.…”

Section: Communicationmentioning

confidence: 65%

“…We have designed new azadipyrromethene ligands that have extended conjugation by installing phenylethynyl groups at the pyrollic positions, and coordinating these ligands with metal(II) complexes to form large conjugated structures with intense red absorption, high electron affi nity and strong accepting properties. [ 13 ] These molecules have conjugated arms pointing in all directions with the potential for isotropic charge transport.…”

Section: Communicationmentioning

confidence: 99%

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Azadipyrromethene‐Based Zn(II) Complexes as Nonplanar Conjugated Electron Acceptors for Organic Photovoltaics

et al. 2014

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The effectiveness of new a electron acceptor for organic solar cells is demonstrated. The acceptor is a homoleptic zinc(II) complex of 2,6-diphenylethynyl-1,3,7,9-tetraphenylazadipyrromethene. The high power-conversion efficiency obtained is attributed to the acceptor's 3D structure, which prevents crystallization and promotes a favourable nanoscale morphology, its high Voc , and its ability to contribute to light harvesting at 600-800 nm.

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Section: Communicationmentioning

confidence: 65%

Section: Communicationmentioning

confidence: 99%

Azadipyrromethene‐Based Zn(II) Complexes as Nonplanar Conjugated Electron Acceptors for Organic Photovoltaics

et al. 2014

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“…To install phenylacetylene groups, iodination of the ADP derivatives was done according to literature procedures and purified by washing with chloroform in good yield [5,33–34]. Stille cross-coupling with the appropriate tributyltin-phenylacetylene analogs afforded the WS3 derivatives in good yield (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…Xylenes and tetrahydrofuran were distilled over sodium and benzophenone, degassed and stored under nitrogen. ADP, ADPI 2 , WS3, BF 2 (WS3), and Zn(WS3) 2 were synthesized and purified according to literature procedures with minor modifications [2,5,9,33–34]. (4-Fluorophenylethynyl)tributyltin (for the synthesis of L3), and [4-(trifluoromethyl)phenyl](tributyltin)acetylene (for the synthesis of L4) were synthesized according to literature procedures with minor modifications and used without purification [35–36].…”

Section: Methodsmentioning

confidence: 99%

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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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Lewis Acid Modulation of meso‐Pyridyl BODIPY Chromophores

Choung

Teets

2018

ChemPhotoChem

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Two pyridyl‐substituted boron dipyrromethene (BODIPY) compounds are shown to interact with the strong Lewis acid B(C6F5)3. The borane adducts are characterized by multinuclear NMR and in one case by X‐ray crystallography. The titration of pyridyl‐substituted BODIPYs with B(C6F5)3 results in a bathochromic shift of the UV/Vis absorption and emission spectra, with the magnitude of the shift depending on the distance of the bound borane from the BODIPY core. In meso‐4‐pyridyl‐BODIPY, binding of B(C6F5)3 induces a small circa 230 cm−1 red shift in the UV/Vis absorption maximum, with a much larger 1950 cm−1 shift in the photoluminescence maximum. In meso‐4‐pyridylphenyl‐BODIPY, where the pyridine Lewis base is separated from the BODIPY core by a phenyl spacer, smaller shifts of circa 120 cm−1 in UV/Vis absorption and 330 cm−1 in photoluminescence are observed. This work shows that these organic chromophores can interact with Lewis acids as a means of systematically perturbing the electronic structure and excited‐state properties.

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Introducing 3D conjugated acceptors with intense red absorption: homoleptic metal(ii) complexes of di(phenylacetylene) azadipyrromethene

Cited by 39 publications

References 61 publications

Azadipyrromethene‐Based Zn(II) Complexes as Nonplanar Conjugated Electron Acceptors for Organic Photovoltaics

Azadipyrromethene‐Based Zn(II) Complexes as Nonplanar Conjugated Electron Acceptors for Organic Photovoltaics

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

Lewis Acid Modulation of meso‐Pyridyl BODIPY Chromophores

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