Organic Photovoltaics Using Tetraphenylbenzoporphyrin Complexes as Donor Layers

Perez, Mauricio D.; Borek, Carsten; Djurovich, Peter I.; Mayo, Elizabeth I.; Lunt, Richard R.; Forrest, Stephen R.; Thompson, Mark E.

doi:10.1002/adma.200802683

Cited by 52 publications

(42 citation statements)

References 29 publications

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“…The shorter and longer N1ÀN2 distances were 2.519(3) and 2.960(3) , respectively, and the shape of the N 4 cavity was rectangular with interior angles of 91.26(8) and 88.74(8)8, at N1 and N2, respectively. The C5 À C6 length was 1.422(4) , which was longer than those of 1 a and 1 c. On the other hand, the C2 À C19 distance was 3.087 (4) , which was about 0.2 shorter than those of 1 a and 1 c. This could be due to the lack of substituents at the C2 and C19 positions.…”

Section: Resultsmentioning

confidence: 86%

“…The crude product was purified by recrystallization from CH 2 Cl 2 /MeOH to give 18 as a yellow powder (0.57 g, 1. 4 191.3, 135.7, 128.1, 124.6, 121.4, 33.0, 29.4, 27.6, 26.9, 26.6, 9.6 …”

Section: Methodsmentioning

confidence: 99%

“…[4] Porphycene, a constitutional isomer of porphyrin, defined as [18]porphyrinA C H T U N G T R E N N U N G (2.0.2.0), was first prepared by Vogel et al [5] in 1986 and has been extensively studied owing to versatile applications as photodynamic therapy (PDT) dyes, catalysts, protein mimics, and so on.…”

Section: Introductionmentioning

confidence: 99%

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First Synthesis of Dodecasubstituted Porphycenes

Kuzuhara

Yamada

Yano

et al. 2011

Chemistry A European J

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The synthesis of dodecasubstituted porphycenes has not been reported, to date. Herein, the preparation of tetramethyloctaethylporphycene by a McMurry-type coupling of 3,3',4,4'-tetraethyl-5,5'-diformyl-2,2'-bipyrrole was attempted at first, but dodecasubstituted porphycene was not successfully obtained and only pyrrolocyclophene was obtained. The structure of the pyrrolocyclophene was determined by (1)H NMR spectroscopy, FAB MS, and X-ray crystal-structure analysis. The pyrrolocyclophene was not successfully oxidized to porphycene. Then, the McMurry-type coupling of bicyclo[2.2.2]octadiene (BCOD)-fused 5,5'-diacyl-2,2'-bipyrroles was performed and tetra-meso-octa-β-substituted (dodecasubstituted) porphycenes were successfully obtained for the first time. The structures were determined by (1)H NMR spectroscopy and X-ray crystal-structure analysis. The crystal structures and NMR spectra were compared carefully with octasubstituted porphycenes, and there was a good correlation between the position of the substituents, the N1−−N2 and N1−−N4 distances of the porphycene inner nitrogen atoms, and NMR chemical shifts of the inner NH protons, which expressed the strength of N−−H⋅⋅⋅N hydrogen bonding between N1 and N2. These results suggested that the BCOD structure was relatively compact compared with common alkyl groups and that was why the dodecasubstituted porphycenes were available this time. UV/Vis absorption and fluorescence properties are also discussed.

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Section: Resultsmentioning

confidence: 86%

“…The crude product was purified by recrystallization from CH 2 Cl 2 /MeOH to give 18 as a yellow powder (0.57 g, 1. 4 191.3, 135.7, 128.1, 124.6, 121.4, 33.0, 29.4, 27.6, 26.9, 26.6, 9.6 …”

Section: Methodsmentioning

confidence: 99%

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First Synthesis of Dodecasubstituted Porphycenes

Kuzuhara

Yamada

Yano

et al. 2011

Chemistry A European J

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“…Although the oxovanadium with diketones is a highly studied liquid crystal known as metallomesogensoxovanadium [7] [8] [9], there are no reports about the study of its optical properties as a thin film. Although there are not too many reports on the preparation of these films by thermal vacuum evaporation [10] [11], the important properties of vanadium have been attributed to the stability of its different oxidation states.…”

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confidence: 99%

Synthesis and Evaluation of the Semiconductor Behavior in Vanadium Indanone Derivatives Thin Films

Lozano-González¹,

Sánchez-Vergara²,

Alvarado-Beltrán³

et al. 2017

AMPC

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In this work, we propose a method to synthesize vanadium (IV) 2-benzyli-dene-1-indanone derivatives, used to prepare film structures by thermal evaporation. The complexes possess high melting point allowing the using of vacuum deposition methods. All the samples were grown at room temperature (25˚C) and low deposition rates (0.4 Å/s). The surface morphology and structure of the deposited films were studied by scanning electron microscopy (SEM) and spectroscopy dispersive energy (EDS). Optical absorption studies of the complex films were performed in the 200 -1100 nm wavelength range. The Tauc band gap (Eg) of the thin films was determined from the (αhν) 1/2 vs. hν plots for indirect transitions. The vanadium (IV) complex films show optical activation energies in the range of organic semiconductors. Multilayer nylon 11/vanadium indanone devices were fabricated using ITO and silver electrodes. The d.c. electrical properties of the device were also investigated. It was found that the temperature-dependent electric current in the structure showed a semiconductor behavior. At lower voltages below 7 V, the current density in the forward direction was found to obey an ohmic I-V relationship; for higher voltages above 7 V, the conduction was dominated by a space-charge-limited (SCLC) mechanism. The electrical activation energies (Ea) of the complexes were in the 2.17 -2.31 eV range.

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“…Devices using PtTPBP have been made and characteristic J-V and EQE spectra of these devices are shown in figure 1(b). 21 The devices perform well, but the gap in absorptivity negatively impacts the J SC . The spectral responsivity of this device illustrates the problem of using a porphyrin, which results in low conversion efficiencies between 500 and 600 nm, figure 1(c).…”

Section: Introductionmentioning

confidence: 99%

Implications of Multichromophoric Arrays in Organic Photovoltaics

et al. 2015

Self Cite

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A covalently linked multi-chromophoric array (BDP-Por) was used as the donor layer in planar hetero-junction organic photovoltaic (OPV) cells with the structure (ITO/BDPPor/C 60 /BCP//Al, BCP = bathocuproine). BDP-Por is a platinum tetrabenzoporphyrin core (Pt(TPBP)) bonded through the phenyl groups to the meso position of four 4,4-difluoro-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene (BODIPY) moieties. The OPV outperforms analogous OPVs which use only the Pt(TPBP) as the donor, predominantly by producing a higher short circuit current (J SC of 2.5 vs. 4.5 mA/cm 2 ), due to the enhanced absorptivity of the multi-chromophoric array. The open circuit voltages (V OC ) for Pt(TPBP) and BDP-Por based OPVs are both 0.65 volts. The system was further investigated by preparing and testing OPVs made from an analogous system with porphyrin and BODIPY components blended into a single homogeneous donor layer that absorbs similarly to the array. It is then found that the mixed system generates the same photocurrent as the array with a similar responsivity, but gives an unstable open circuit voltage that quickly degrades to 0.34 V. It is determined that the donor layer components undergo phase segregation at the interface upon illumination, resulting in the decreased voltage and highlighting an advantage of the multi-chromophoric array.

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Organic Photovoltaics Using Tetraphenylbenzoporphyrin Complexes as Donor Layers

Cited by 52 publications

References 29 publications

First Synthesis of Dodecasubstituted Porphycenes

First Synthesis of Dodecasubstituted Porphycenes

Synthesis and Evaluation of the Semiconductor Behavior in Vanadium Indanone Derivatives Thin Films

Implications of Multichromophoric Arrays in Organic Photovoltaics

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