Small molecule BODIPY dyes as non-fullerene acceptors in bulk heterojunction organic photovoltaics

Poe, Ambata; Pelle, Andrea M. Della; Subrahmanyam, Ayyagari V.; White, William; Wantz, Guillaume; Thayumanavan, S.

doi:10.1039/c3cc49648a

Cited by 79 publications

(57 citation statements)

References 31 publications

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“…This study was conducted by Poe et al. in which they synthesized a series of A−D−A small molecules containing terminal BODIPY π‐ units . BODIPY moieties were conjugated through their meso ‐positions using a brominated hexylthiophene linker to afford 30, 31 and 32 (Figure ).…”

Section: Introductionmentioning

confidence: 99%

“…There is only one example of a BODIPY semiconductor showing a charge carrier mobility of >0.1 cm 2 V −1 s −1 . BODIPY π‐core possesses a unique electronic structure and its π‐architecture has a clear impact on its charge‐carrier type ,,. While π‐extension on the BODIPY's meso ‐position leads to n ‐channel semiconducting characteristics, aromatic substitutions at other positions result in p ‐channel transistor behavior .…”

Section: Introductionmentioning

confidence: 99%

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BODIPY‐Based Semiconducting Materials for Organic Bulk Heterojunction Photovoltaics and Thin‐Film Transistors

Özdemir

Kim

et al. 2018

ChemPlusChem

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The rapid emergence of organic (opto)electronics as a promising alternative to conventional (opto)electronics has been achieved through the design and development of novel π‐conjugated systems. Among various semiconducting structural platforms, 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) π‐systems have recently attracted attention for use in organic thin‐films transistors (OTFTs) and organic photovoltaics (OPVs). This Review article provides an overview of the developments in the past 10 years on the structural design and synthesis of BODIPY‐based organic semiconductors and their application in OTFT/OPV devices. The findings summarized and discussed here include the most recent breakthroughs in BODIPYs with record‐high charge carrier mobilities and power conversion efficiencies (PCEs). The most up‐to‐date design rationales and discussions providing a strong understanding of structure‐property‐function relationships in BODIPY‐based semiconductors are presented. Thus, this review is expected to inspire new research for future materials developments/applications in this family of molecules.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

BODIPY‐Based Semiconducting Materials for Organic Bulk Heterojunction Photovoltaics and Thin‐Film Transistors

Özdemir

Kim

et al. 2018

ChemPlusChem

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“…[14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] Only in the last two years, larger PCEs (4-6%) have been reported. However, both systems normally show poor PCEs o3% or around 3%.…”

Section: Introductionmentioning

confidence: 99%

A perylene diimide (PDI)-based small molecule with tetrahedral configuration as a non-fullerene acceptor for organic solar cells

et al. 2015

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In this paper, a new perylene diimide (PDI)-based acceptor Me-PDI 4 with tetrahedral configuration (or 3D) has been synthesized and characterized. Solution-processed organic solar cells (OSCs) based on Me-PDI 4 have been investigated and our results show that the device performance can reach as high as 2.73%. Our new design with tetrahedral configuration (or 3D) could be an efficient approach to increase the PCE of OSCs with non-fullerene acceptors.

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“…The D–A structure is the most employed structure for tuning absorption of BODIPY. Absorptions of electron‐rich groups, such as triphenylamine, carbazole, fluorene and cyclopentadithiophene, combined with electron‐deficient BODIPY have been reported . Besides the D–A structure, donor–acceptor–donor (D–A–D) triad is also attractive because it offers the increase in cross‐section absorption and nonlinear optical behavior .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, optical, and electrochemical properties, and theoretical calculations of BODIPY containing triphenylamine

Wanwong

Surawatanawong

Khumsubdee

et al. 2016

Heteroatom Chemistry

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The boron dipyrromethene (BODIPY) triads consisting of two triphenylamine units as electron donor (D) and BODIPY core as electron acceptor (A; B3, and B4) have been synthesized using facile palladium cross‐coupling reactions to broaden the absorption of the BODIPY dyes. All dyes and intermediates were characterized by 1H NMR, 11B NMR, 13C NMR, and 19F NMR spectroscopies, UV–Vis spectroscopy, fluorescence spectroscopy, cyclic voltammetry, and time‐dependent density functional theory calculations. It was found that an increase in conjugation to the BODIPY core systematically extended the absorption and emission wavelength maxima. As a consequence, B4 containing the D–π–A–π–D structure, exhibited the longest absorption and emission maxima at 597 and 700 nm, respectively, with 1.8 eV in optical bandgap. The 96 nm red‐shifted absorption of B4 as compared to the unsubstituted BODIPY (B1) indicated the effective electronic communication between triphenylamine and BODIPY. This suggested that the proper alignment of triphenylamine and BODIPY triad could lead to broader absorption and suitable low energy bandgap. Furthermore, the molecular modeling has been employed to analyze the electronic and optical properties of the dyes. We found that the optical, electrochemical, and theoretical bandgaps of all dyes were in good agreement.

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Small molecule BODIPY dyes as non-fullerene acceptors in bulk heterojunction organic photovoltaics

Cited by 79 publications

References 31 publications

BODIPY‐Based Semiconducting Materials for Organic Bulk Heterojunction Photovoltaics and Thin‐Film Transistors

BODIPY‐Based Semiconducting Materials for Organic Bulk Heterojunction Photovoltaics and Thin‐Film Transistors

A perylene diimide (PDI)-based small molecule with tetrahedral configuration as a non-fullerene acceptor for organic solar cells

Synthesis, optical, and electrochemical properties, and theoretical calculations of BODIPY containing triphenylamine

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