An efficient non-fullerene acceptor based on central and peripheral naphthalene diimides

Rao, P. Srinivasa; Gupta, Akhil; Srivani, Doli; Bhosale, Sidhanath V.; Bilić, Ante; Li, Jingliang; Xiang, Wanchun; Evans, Richard A.; Bhosale, Sheshanath V.

doi:10.1039/c8cc01779d

Cited by 27 publications

(10 citation statements)

References 24 publications

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“…Aryl imides are an important class of materials and have found extensive use in organic electronic applications. − These building blocks are routinely incorporated into both molecular − and polymeric − designs typically for their electron deficient character and self-assembly properties. Among them, the rylene-based imides, perylene and naphthalene diimide (PDI, NDI, respectively), have found great success as electron transporting materials in organic field-effect transistors (OFETs) − and organic solar cells (OSCs). − Until recently, N -(alkyl)benzothioxanthene-3,4-dicarboximide (BTXI), a sulfur containing rylene imide dye used in bioimaging , and for its antitumor activity, had not been considered as a building block for use in organic electronics. Cabanetos et al demonstrated an efficient selective bromination of the BTXI dye that shows excellent compatibility among commonly used palladium catalyzed C–C bond forming reactions including Stille, Suzuki, and Sonagashira, as well as the atom economical direct (hetero)arylation (DHA) …”

Section: Introductionmentioning

confidence: 99%

Donor or Acceptor? How Selection of the Rylene Imide End Cap Impacts the Polarity of π-Conjugated Molecules for Organic Electronics

Payne

Rice

McAfee

et al. 2018

ACS Appl. Energy Mater.

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Three molecular semiconductors are compared and evaluated in organic field-effect transistors and organic solar cells. The molecules are constructed from the dyes diketopyrrolopyrrole (DPP), perylene diimide (PDI), and N-(alkyl)benzothioxanthene-3,4-dicarboximide (BTXI). The compound PDI–DPP–PDI (1) has previously been reported and used as a nonfullerene acceptor. The compounds PDI–DPP–BTXI (2) and BTXI–DPP–BTXI (3) were synthesized using direct (hetero)arylation methods and fully identified using NMR spectroscopy and mass spectrometry. All three compounds were characterized using UV–visible spectroscopy, cyclic voltammetry, and density functional theory calculations. Increasing the BTXI content results in a progressive destabilization of the electronic energy levels. For all compounds, no significant changes in the optical absorption spectra are observed when compared to a combination of the constituent optical absorption spectra. Compound 1 exhibits electron transport characteristics and functions as an electron acceptor in solar cells that produce a power conversion efficiency of 5%. Compound 2 exhibits unbalanced (electron transporting dominate) ambipolar charge transport characteristics and performs better as a nonfullerene acceptor in solar cells. Compound 3 exhibits balanced ambipolar charge transport characteristics and performs best as a donor in solar cell devices. The ability to tune the optical and charge-carrier transport characteristics of these panchromatic dyes through direct (hetero)arylation synthesis offers a distinctive way to create organic semiconductors that span a range of device performance metrics.

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Section: Introductionmentioning

confidence: 99%

Donor or Acceptor? How Selection of the Rylene Imide End Cap Impacts the Polarity of π-Conjugated Molecules for Organic Electronics

Payne

Rice

McAfee

et al. 2018

ACS Appl. Energy Mater.

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“…The synthesis of required starting materials such as 2‐Br‐th‐NDI ( 1 ) [24c] and 4‐ethynyl‐N,N‐diphenylaniline (TPAA) ( 2 ) [26] were achieved by literature reported methods (Scheme 1). NDI‐TPA‐1 to NDI‐TPA‐6 were synthesized according to previous literature reports [11–18] .…”

Section: Resultsmentioning

confidence: 99%

The Effect of TCNE and TCNQ Acceptor Units on Triphenylamine‐Naphthalenediimide Push‐Pull Chromophore Properties

et al. 2021

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Asymmetrical and symmetrical push‐pull chromophore‐based on triphenylamine (TPA) donors and naphthalenediimide (NDI) acceptors are designed and successfully synthesized via [2+2] cycloaddition‐retroelectrocyclization (CA‐RE) reaction with well‐known electron‐accepting tetracyanoethylene (TCNE) and 7,7,8,8, ‐tetracyanoquinodimethane (TCNQ) groups. The novel series of compounds NDI‐TPA‐1 to NDI‐TPA‐6 were characterized to identify the influence of the TCNE and TCNQ π‐conjugated linkers on the optical, electrochemical, and electronic properties of these molecules. We found that in dichloromethane the NDI‐TPAs 1, 4, 5, and 6 display absorbance peaks at increasing wavelengths 605, 641, 646, and 645 nm, respectively. We demonstrated that through simple chemical modification we could drop the lowest occupied molecular orbital of NDI‐TPA‐1 to 6. Furthermore, NDI‐TPA‐1 to 6 were integrated into organic thin‐film transistors (OTFTs) via spin‐coating technique, and charge transfer properties were investigated. We found that the choice of the functional group led to either p‐type, n‐type, or ambipolar characteristics.

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“…lipophilic, hydrophilic, alkoxy, aliphatic with terminal thiol groups, and polyethylene glycol, at imide positions enhances the solubility of a proposed target, a result that is of great significance to generate excellent pristine and blend films of the proposed target material without crystallisation. [79][80][81][82] Therefore, it is timely to review the literature of ETL materials based on NDI functionality and to correlate the structural features with the device performance in order to determine useful design concepts to advance the area. This review provides the current state-of-the-art in the field of ETL materials, both polymers and small molecules, comprising NDI functionality for PSCs and describes structure-property relationships.…”

Section: Ndi-based Electron Transport Layer Materialsmentioning

confidence: 99%

Naphthalene diimide-based electron transport materials for perovskite solar cells

et al. 2021

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An efficient non-fullerene acceptor based on central and peripheral naphthalene diimides

Cited by 27 publications

References 24 publications

Donor or Acceptor? How Selection of the Rylene Imide End Cap Impacts the Polarity of π-Conjugated Molecules for Organic Electronics

Donor or Acceptor? How Selection of the Rylene Imide End Cap Impacts the Polarity of π-Conjugated Molecules for Organic Electronics

The Effect of TCNE and TCNQ Acceptor Units on Triphenylamine‐Naphthalenediimide Push‐Pull Chromophore Properties

Naphthalene diimide-based electron transport materials for perovskite solar cells

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