Fabrication and Performance of Copper Phthalocyanine/Squaraine Dye/Perylene Composite with Bulk Heterojunctions by the Solution Blending Process

Chen, Chien‐Hsun; Cheng, Wen-Tung; Tsai, Ming-Liao; Huang, Kou-Tung

doi:10.1021/ie201586b

Cited by 11 publications

(8 citation statements)

References 32 publications

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“…In this paper we will investigate the photophysical properties of heterodimer and heterotrimer SCs built up from an indolenine squaraine dye and a BODIPY dye. The former were chosen as they display sharp and intense absorption bands in the red to near-infrared spectral region − and they are being used in numerous applications such as in biolabeling, − ion recognition, − nonlinear optics − and solar energy conversion. − BODIPY dyes are even more popular as fluorescence dyes absorbing in the green spectral region. They also show a relatively intense and narrow absorption band. − These are ideal conditions for investigating chromophore interactions in SCs because coupling induced shifts will easily be visible for strong and narrow absorption bands.…”

Section: Introductionmentioning

confidence: 99%

Coupled Oscillators for Tuning Fluorescence Properties of Squaraine Dyes

Lambert¹,

Scherpf²,

Ceymann³

et al. 2015

J. Am. Chem. Soc.

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Combining a squaraine (S) and a BODIPY (B) chromophore in a heterodimer (SB) and two heterotrimers (BSB and SBS) by alkyne bridges leads to the formation of coupled oscillators whose fluorescence properties are superior compared to the parent squaraine chromophore. The lowest energy absorption and emission properties of these superchromophores are mainly governed by the squaraine part and are shifted by more than 1000 cm(-1) to the red by excitonic interaction between the squaraine and the BODIPY dye. Employing polarization-dependent transient absorption and fluorescence upconversion measurements, we could prove that the lowest energy absorption in SB and BSB is caused by a single excitonic state but by two for SBS. Despite the spectral red-shift of their lowest absorption band, the fluorescence quantum yields increase for SB and BSB compared to the parent squaraine chromophore SQA. This is caused by intensity borrowing from the BODIPY states, which increases the squared transition moments of the lowest energy band dramatically by 29% for SB and 63% for BSB compared to SQA. Thereby, exciton coupling leads to a substantial enhancement of fluorescence quantum yield by 26% for SB and by 46% for BSB and shifts the emission from the red into the near-infrared. In this way, the BODIPY-squaraine conjugates combine the best properties of each class of dye. Thus, exciton coupling in heterodimers and -trimers is a valuable alternative to tuning fluorescence properties by, e.g., attaching substituents to chromophores.

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Section: Introductionmentioning

confidence: 99%

Coupled Oscillators for Tuning Fluorescence Properties of Squaraine Dyes

Lambert¹,

Scherpf²,

Ceymann³

et al. 2015

J. Am. Chem. Soc.

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“…Thus, our aim was to synthesize a copolymer built up from two different chromophores which are covalently connected but which nevertheless shows J-type optical properties and thus may serve as a model for a hetero-J-aggregate. To reach this goal, we used squaraine dyes because these are similar to cyanine dyes with respect to their absorption and fluorescence properties but, unlike those, are neutral and allow the synthesis of homopolymers by standard procedures such as Suzuki or Yamamoto coupling reactions. − Furthermore, squaraine dyes attracted recent interest because of their optical properties that combine a sharp absorption in the red to near-infrared spectral region with high fluorescence quantum yields. − Besides their use as biolables, − photoconductors, compounds for data imaging, ion sensors, − NIR emitters in thin-film dye-doped organic light-emitting diodes, and in nonlinear optics, − squaraine dyes also proved useful for photovoltaic applications ,− because of their favorable absorption in the red region of the visible solar spectrum. However, in this context the relatively narrow bandwidth of their absorption is a drawback.…”

Section: Introductionmentioning

confidence: 99%

Singlet–Singlet Exciton Annihilation in an Exciton-Coupled Squaraine-Squaraine Copolymer: A Model toward Hetero-J-Aggregates

et al. 2014

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Low-band-gap polymers with broad spectral absorption are highly sought after for application in organic photovoltaic cells and other optoelectronic devices. Thus, a conjugated copolymer based on two different indolenine squaraine dyes SQA and SQB was synthesized by Suzuki coupling, and its steady-state and time-resolved optical properties were investigated in detail. In CHCl3 the copolymer [SQA-SQB] n shows a strongly broadened and red-shifted absorption compared to that of its monomers, which was explained by exciton coupling of localized transition moments. The theoretical background of exciton coupling theory for copolymers was worked out in detail. In toluene, [SQA-SQB] n displays a spectral narrowing of the lowest excitation band which resembles the exchange narrowing effect found in cyanine J-aggregates. In this way [SQA-SQB] n behaves like a one-dimensional covalently bound hetero-J-aggregate. The photoinduced dynamics of the copolymer was investigated by transient absorption pump–probe spectroscopy with femtosecond resolution. Because of the unusually high exciton diffusion constant, singlet–singlet annihilation is the rate-limiting step for deactivation of the copolymer in solution at high laser fluencies. This is unlike the situation for many conjugated polymers in the solid state, where diffusion-limited annihilation is usually found. Thus, the [SQA-SQB] n copolymer is a unique model system which combines the excitonic features of J-aggregates with the chemical robustness of a polymer.

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“…Pc constitutes a group of heterocyclic compounds with four isoindole-class [(C 6 H 4 )C 2 N] units linked by four N atoms to form a conjugated macrocyclic chain, a number of Pc are modified in the center with various metal elements, including Cu, Zn, Pb, etc., and substituted in the periphery with various groups [34,35,36,37]. Metal phthalocyanine has been widely used in optical, conducting, and magnetic materials; dye-sensitized solar cells; organic thin-film transistors; organic light-emitting devices; fuel cells; catalysis; sensors; and photodynamic therapy [38,39,40]. Pb and Pb-containing inorganic or organic compounds are most commonly used as high-energy ray radiation protection materials because of their low cost and excellent properties of radiation shielding.…”

Section: Introductionmentioning

confidence: 99%

Amino-Functionalized Lead Phthalocyanine-Modified Benzoxazine Resin: Curing Kinetics, Thermal, and Mechanical Properties

Gao

Pan

et al. 2019

Polymers

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Phenol-diaminodiphenylmethane-based benzoxazine (P-ddm)/phthalocyanine copolymer was prepared by using P-ddm resin as matrix and 3,10,17,24-tetra-aminoethoxy lead phthalocyanine (APbPc) as additive. Fourier-transform infrared (FTIR), differential scanning calorimetry (DSC), dynamic mechanical analysis (DMA), and thermogravimetric analysis (TGA) were used to investigate the curing behavior, curing kinetics, dynamic mechanical properties, thermal stability, and impact strength of the prepared copolymers. The kinetic parameters for the P-ddm/APbPc blend curing processes were examined by utilizing the iso-conversional, Flynn–Wall–Ozawa, and Málek methods. The P-ddm/APbPc blends exhibit two typical curing processes, and DSC results confirmed that the blending of APbPc monomer can effectively reduce the curing temperature of P-ddm resin. The autocatalytic models also described the non-isothermal curing reaction rate well, and the appropriate kinetic parameters of the curing process were obtained. The DMA and impact strength experiments proved that the blending of APbPc monomer can significantly improve the toughness and stiffness of P-ddm resin, the highest enhancements were observed on 25 wt.% addition of APbPc, the recorded values for the storage modulus and impact strength were 1003 MPa and 3.60 kJ/m2 higher, respectively, while a decline of 24.6 °C was observed in the glass transition temperature values. TGA curves indicated that the cured copolymers also exhibit excellent thermal stabilities.

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Fabrication and Performance of Copper Phthalocyanine/Squaraine Dye/Perylene Composite with Bulk Heterojunctions by the Solution Blending Process

Cited by 11 publications

References 32 publications

Coupled Oscillators for Tuning Fluorescence Properties of Squaraine Dyes

Coupled Oscillators for Tuning Fluorescence Properties of Squaraine Dyes

Singlet–Singlet Exciton Annihilation in an Exciton-Coupled Squaraine-Squaraine Copolymer: A Model toward Hetero-J-Aggregates

Amino-Functionalized Lead Phthalocyanine-Modified Benzoxazine Resin: Curing Kinetics, Thermal, and Mechanical Properties

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