Rational design of π-bridges for ambipolar DPP-RH-based small molecules in organic photovoltaic cells

Eom, Yoonho; Song, Chang Eun; Shin, Won Suk; Lee, Sang Kyu; Lim, Eunhee

doi:10.1016/j.jiec.2016.10.001

Cited by 23 publications

(10 citation statements)

References 45 publications

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“…At high FeCl 3 concentration, the decrease of polaron state peak at 832 nm indicates that the speed of polaron state P3HT converted to the bipolaron state is higher than that of polaron state P3HT generated. The band gaps obtained from the UV-vis-NIR spectra of pristine DPPTTT and P3HT were 1.28 eV and 1.9 eV (Figure S4), respectively, which are consistent with previously reported works [37][38][39][40][41][42] .…”

Section: Electrical Conductivity and Seebeck Coefficient Ofsupporting

confidence: 91%

“…(3) E HOMO = -(4.8 -E 1/2Ferrocene + φ ox ) where is the average of the oxidation peak potential and the E 1/2Ferrocene reduction peak of the internal reference, ferrocene (shown in Figure S5). The obtained HOMO values are similar to the reported values in previous literature, -5.2 eV for P3HT 37,38 , and -5.2 eV for DPPTTT [40][41][42] Based on these results, we believe that the polarity switching of DPPTTT films from p-to n-type is due to the crossing of Fermi level (E F ) from above the HOMO (valence band, E v ) to below the HOMO. The hopping model reported by Fritzsche was typically used to describe the charge carrier transport in conducting polymers.…”

Section: Electrical Conductivity and Seebeck Coefficient Ofsupporting

confidence: 89%

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P-Type Chemical Doping-Induced High Bipolar Electrical Conductivities in a Thermoelectric Donor–Acceptor Copolymer

Wang

et al. 2021

CCS Chem

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Conducting polymers typically transfer either electrons or holes. It is rare to see high bipolar (p-and n-type) electrical conductivities within a single bulk doped organic polymer without the assistant of gate voltage. Here, we report that FeCl 3 doped solution-processable D-A copolymer poly (2,5-bis(2octyldodecyl)-3,6-di(thiophen-2-yl)diketopyrrolo [3,4-c] pyrrole-1,4-dione-altthieno[3,2-b]thiophen) (DPPTTT) could exhibit a high p-type electrical conductivity of 130.6 S/cm and a good n-type electrical conductivity of 14.2 S/cm when engineering the doping level. Both the p-and n-type electrical conductivities are superior to that of most of the solution-processable D-A copolymers including monopolar polymers. The high electrical conductivity results in high thermoelectric performance of DPPTTT in both p-and n-type, which also leads to a high current density of 3 A/cm 2 for a fully organic planar p-n junction created with only one material. Structural and spectroscopic tests have been performed to provide a fundamental understanding of the polarity switching mechanism. The results open the opportunity of making p-and n-type modules with a single conducting polymer for future modern organic electronics.This study may arouse the interest of researchers in exploring novel conducting polymers and enrich the knowledge of charge transport in organic materials.

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Section: Electrical Conductivity and Seebeck Coefficient Ofsupporting

confidence: 91%

Section: Electrical Conductivity and Seebeck Coefficient Ofsupporting

confidence: 89%

P-Type Chemical Doping-Induced High Bipolar Electrical Conductivities in a Thermoelectric Donor–Acceptor Copolymer

Wang

et al. 2021

CCS Chem

View full text Add to dashboard Cite

show abstract

“…At high FeCl3 concentration, the decrease of polaron state peak at 832 nm indicates that the speed of polaron state P3HT converted to the bipolaron state is higher than that of polaron state P3HT generated. The band gaps obtained from the UV-vis-NIR spectra of pristine DPPTTT and P3HT were 1.28 eV and 1.9 eV (Figure S4), respectively, which are consistent with previously reported works 39,40,41,42,43,44 .…”

Section: Resultssupporting

confidence: 91%

“…where 1/2 is the average of the oxidation peak potential and the reduction peak of the internal reference, ferrocene (shown in Figure S5). The obtained HOMO values are similar with the reported values in previous literature, -5.2 eV for P3HT 39,45 and -5.2 eV for DPPTTT 43,46,47 . The LUMO values for DPPTTT and P3HT were calculated based on the CV results and the optical band gap to be -3.91 eV and -3.26 eV, respectively.…”

Section: Resultssupporting

confidence: 90%

Polarity switching from p- to n-type in a single thermoelectric donor-acceptor copolymer by p-type doping

Wang

et al. 2021

Preprint

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The transport mechanism of organic materials is still far away from being well understood and controlled although conducting polymers have been discovered since 1977. It is rare to see conducting polyers possessing high bipolar (p- and n-type) electrical conductivities within a single bulk doped organic polymer without the assistant of gate voltage. Here, we report a novel approach to provide high performance n-type materials by p-type doping. More importantly, the bipolar electrical conductivities of the donor-acceptor conducting polymer are high, resulting high bipolar power factors among the solution-processable ambipolar D-A copolymers. A fully organic p-n junction is created in a planar film, exhibiting a high rectification ratio of 2 x 102 at +5 V with a high current density of 3 A/cm2. Structural and spectroscopic tests have been performed to provide a fundamental understanding of the polarity switching mechanism. The results open the opportunity of making p- and n-type modules with a single conducting polymer for future modern organic electronics.

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“…25 Very recently, an ambipolar optoelectronic molecule, containing the strong electron-withdrawing units of DPP and 3-ethylrhodanine (RD), has been designed and explored in the organic solar cells. 26−28 However, there are few examples of using π-conjugated organic semiconducting molecules as photocatalysts for the degradation of organic pollutants under visible light irradiation. Recently, the composited organic photocatalyst obtained through π–π interactions of 7,7,8,8-tetracyanoquinodimethane and perylene tetracarboxylic diimide was reported to show high efficiency for the visible light-irradiated degradation of phenol.…”

Section: Introductionmentioning

confidence: 99%

Metal-Free Organic Optoelectronic Molecule as a Highly Efficient Photocatalyst for the Degradation of Organic Pollutants

Zhang

Sun

et al. 2019

ACS Omega

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With the increasing consumption of natural resources, photocatalysis converting solar energy to chemical energy has attracted extensive attention of researchers owing to the advantages of developing energy-saving and environmentally benign processes. In this work, a facile and simple method was developed to synthesize a metal-free organic optoelectronic molecule (denoted as DPPRD), which is composed of a central diketopyrrolopyrrole moiety and two terminal units of a rhodanine (RD) moiety. This is a first green strategy toward the synthesis of DPPRD. Because of good thermal stability, narrow band gap, and excellent visible light absorption of solar spectrum, DPPRD exhibited to be an efficient and chemically stable photocatalyst for visible light degradation of organic pollutants such as bisphenol A (BPA) and methyl orange (MO) in aqueous solution. The control experiments with different types of radical scavengers implied that the hole (h + ) and hydroxyl radicals ( • OH) were the key reactive species during the photodegradation processes. The photodegradation pathways of BPA and MO were thus proposed based on the identified intermediates. This improved method for DPPRD synthesis is expected to widen its applications to industrial production, whereas its excellent visible light photocatalytic activity would be utilized potentially in the field of environmental and industrial applications.

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Rational design of π-bridges for ambipolar DPP-RH-based small molecules in organic photovoltaic cells

Cited by 23 publications

References 45 publications

P-Type Chemical Doping-Induced High Bipolar Electrical Conductivities in a Thermoelectric Donor–Acceptor Copolymer

P-Type Chemical Doping-Induced High Bipolar Electrical Conductivities in a Thermoelectric Donor–Acceptor Copolymer

Polarity switching from p- to n-type in a single thermoelectric donor-acceptor copolymer by p-type doping

Metal-Free Organic Optoelectronic Molecule as a Highly Efficient Photocatalyst for the Degradation of Organic Pollutants

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