Synthesis, characterization and photovoltaic properties of azadipyrromethene-based acceptors: effect of pyrrolic substituents

Senevirathna, Wasana; Liao, Jiayu; Mao, Zhenghao; Gu, Jun; Porter, Matthew; Wang, Chunlai; Fernando, Roshan; Sauvé, Geneviève

doi:10.1039/c4ta05765a

Cited by 33 publications

(41 citation statements)

References 43 publications

(56 reference statements)

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“…The synthesis of ADP was carried out according to literature procedures [9,33]. The ADP-analogs with fluorine at the proximal or distal phenyl positions (L1-ADP and L2-ADP) were synthesized in a similar fashion with the respective fluorinated chalcones (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…a) Azadipyrromethene ligand labeling positioning; b and c) chelates; d) estimated HOMO/LUMO energy levels [9]. …”

Section: Introductionmentioning

confidence: 99%

“…We have shown that derivatives of Zn(ADP) 2 are promising electron acceptors for organic photovoltaics (OPVs) [9–10]. A series of zinc(II) derivatives with various pyrrolic substitutions showed power conversion efficiencies (PCEs) ranging from 2.2–4.1% when blended with poly(3-hexylthiophene) (P3HT), and the highest PCE was obtained with Zn(WS3) 2 , shown in Fig.…”

Section: Introductionmentioning

confidence: 99%

“…A series of zinc(II) derivatives with various pyrrolic substitutions showed power conversion efficiencies (PCEs) ranging from 2.2–4.1% when blended with poly(3-hexylthiophene) (P3HT), and the highest PCE was obtained with Zn(WS3) 2 , shown in Fig. 1 [9–10]. In comparison, free ligands and BF 2 + chelates showed negligible power conversion efficiencies, and Zn(ADP) 2 gave a maximum efficiency of 1.4% [11].…”

Section: Introductionmentioning

confidence: 99%

“…Chelation with zinc(II) lowers the tendency to self-aggregate, but Zn(ADP) 2 still shows some large aggregates in blend films [10]. The addition of pyrrolic phenylacetylene substituents further helped to break the aggregation and to create a favorable nanoscale phase separation in blend films, leading to higher PCEs [9–10]. DFT calculations show that Zn(WS3) 2 is a very large and non-planar molecule with low electron transfer reorganization energy, further supporting its potential to replace fullerenes in OPVs [12].…”

Section: Introductionmentioning

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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Section: Resultsmentioning

confidence: 99%

“…a) Azadipyrromethene ligand labeling positioning; b and c) chelates; d) estimated HOMO/LUMO energy levels [9]. …”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

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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Femtosecond Spectroscopy and Nonlinear Optical Properties of aza‐BODIPY Derivatives in Solution

Chang

Bondar

Munera

et al. 2022

Chemistry A European J

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The fast relaxation processes in the excited electronic states of functionalized aza‐boron‐dipyrromethene (aza‐BODIPY) derivatives (1–4) were investigated in liquid media at room temperature, including the linear photophysical, photochemical, and nonlinear optical (NLO) properties. Optical gain was revealed for nonfluorescent derivatives 3 and 4 in the near infrared (NIR) spectral range under femtosecond excitation. The values of two‐photon absorption (2PA) and excited‐state absorption (ESA) cross‐sections were obtained for 1–4 in dichloromethane using femtosecond Z‐scans, and the role of bromine substituents in the molecular structures of 2 and 4 is discussed. The nature of the excited states involved in electronic transitions of these dyes was investigated using quantum‐chemical TD‐DFT calculations, and the obtained spectral parameters are in reasonable agreement with the experimental data. Significant 2PA (maxima cross‐sections ∼2000 GM), and large ESA cross‐sections ∼10−20 m2 of these new aza‐BODIPY derivatives 1–4 along with their measured high photostability reveal their potential for photonic applications in general and optical limiting in particular.

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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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Synthesis, characterization and photovoltaic properties of azadipyrromethene-based acceptors: effect of pyrrolic substituents

Abstract: A structure–property study of non-fullerene acceptors based on azadipyrromethene derivatives was performed. Power conversion efficiencies between 2 and 4% were obtained when blended with poly(3-hexylthiophene) as the donor.

Cited by 33 publications

References 43 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

Femtosecond Spectroscopy and Nonlinear Optical Properties of aza‐BODIPY Derivatives in Solution

Lewis Acid Modulation of meso‐Pyridyl BODIPY Chromophores

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