Phthalimide end-capped thienoisoindigo and diketopyrrolopyrrole as non-fullerene molecular acceptors for organic solar cells

Josse, Pierre; Dalinot, Clément; Jiang, Yue; Dabos‐Seignon, Sylvie; Roncali, Jean; Blanchard, Philippe; Cabanetos, Clément

doi:10.1039/c5ta09171c

Cited by 71 publications

(43 citation statements)

References 71 publications

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“…The film morphology would change from edge‐on orientation to more face‐on packing, which was beneficial for the charge transport. In the same year, Cabanetos and co‐workers developed a novel nonfullerene small molecule acceptor A18, consisted of one DPP core, two thiophene units and two ethynyl group linkers as well as two PhI terminal groups. This molecule showed an absorption scope from 500 to 650 nm, and possessed a low‐lying LUMO energy level of −4.13 eV due to the strong electron‐withdrawing groups of PhI and DPP.…”

Section: Nonfullerene Small Molecule Acceptorsmentioning

confidence: 99%

Recent Advances in Nonfullerene Acceptors for Organic Solar Cells

Liu

Hou

et al. 2017

Macromol. Rapid Commun.

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Recently, research on nonfullerene acceptors in organic solar cells has gradually become a hot topic due to such superior characteristics of light absorption and energy-level-convenient manipulation, multiformity of the photoactive material structures, as well as the extensive area in production compared to the fullerene derivatives. However, the nonfullerene acceptors evolved slowly before 2012 and, as a matter of fact, the power conversion efficiency values could only bear 2.0%. Strikingly, nonfullerene acceptors have developed at a fast pace since 2013, with the best device performance of 13.1% now. In this review, recent research progress on nonfullerene acceptors, including small molecules and polymers, are sorted and summarized on the basis of the different characteristics.

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Section: Nonfullerene Small Molecule Acceptorsmentioning

confidence: 99%

Recent Advances in Nonfullerene Acceptors for Organic Solar Cells

Liu

Hou

et al. 2017

Macromol. Rapid Commun.

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“…In contrast, ethyl‐substituted crystalline analogue 14 yielded maximal PCE of 0.99 % in inverted cells and 1.56 % in conventional cells (Table , Figure ). In comparison, the highest PCE reported with a DPP derivative with a single DPP unit is 3.30 % with P3HT as donor . While these results were not the best reported with this chromophore type, the comparative study nonetheless yielded insightful results.…”

Section: Molecular Glasses In Organic Photovoltaicsmentioning

confidence: 86%

Revisiting the Optimal Nano‐Morphology: Towards Amorphous Organic Photovoltaics

Nunzi

Lebel

2018

The Chemical Record

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Organic photovoltaic cells commonly use an active layer with a polycrystalline bulk heterojunction. However, for simplifying the fabrication process, it may be worthwhile to use an amorphous active layer to lessen the burden on processing to achieve optimal performance. While polymers can adopt amorphous phases, molecular glasses, small molecules that can readily form glassy phases and do not crystallize over time, offer an appealing alternative, being monodisperse species. Our group has developed a series of reactive molecular glasses that can be covalently bonded to chromophores to form glass‐forming adducts, and this strategy has been used to synthesize glass‐forming donor and acceptor materials. Herein, the results of devices incorporating these materials in either partially or fully amorphous active layers are summarized. Additionally, these molecular glasses can be used as ternary components in crystalline systems to enhance efficiency without perturbing the morphology.

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“…[11] The planar core of these compounds (Figure 1) consists of a π-conjugated dilactam system which can be substituted with different aromatic groups at the 3-and 6-positions, and with alkyl derivatives as the Nsubstituents. [12,13] Thus, the compounds present a multitude of opportunities for structural and electronic modification via synthetic functionalization, such as end capping of the aromatic sections, [14,15] the addition of conjugated flanking units to extend charge delocalization [16,17] and solubilizing chains of varying polarity at the N position to aid processing. [18] This alkylation of DPP derivatives gives rise to solubility in relatively low polarity organic solvents, [19][20][21] as well as solubility in more polar solvents when heteroatom-containing chains are appended.…”

Section: Introductionmentioning

confidence: 99%

Ground and Excited States of Bis‐4‐Methoxybenzyl‐Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies

et al. 2019

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A series of symmetrically bis‐4‐methoxybenzyl (4MB) N‐substituted 1,4‐diketopyrrolo[3,4‐c]pyrrole (DPP) derivatives have been synthesized. The 4MB unit makes the DPP core soluble, and shows subtle modification of up to 0.2 eV in ground and excited states of the core when compared with related alkyl derivatives. Absorption and emission spectroscopy, as well as electrochemical and computational methods have been employed to prove the importance of the peripheral aryl units on the donor/ acceptor properties of the molecules. The 4MB products are highly fluorescent (quantum yields approaching 100 % in solution), with a unique distribution of frontier states shown by spectroelectrochemistry. The solid‐state fluorescence correlates with the X‐ray crystal structures of the compounds, a Stokes shift of approximately 80 nm is seen for two of the compounds. The frontier energy levels show that this subtle substitutional change could be of future use in molecular energy level tailoring in these, and related, materials for organic (opto)electronics.

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Phthalimide end-capped thienoisoindigo and diketopyrrolopyrrole as non-fullerene molecular acceptors for organic solar cells

Abstract: Two acetylene-bridged molecules, built by grafting phthalimides on thienoisoindigo (TII) and diketopyrrolopyrrole (DPP) blocks, have been synthesized, characterized and evaluated as electron acceptor materials in air-processed inverted organic solar cells.

Cited by 71 publications

References 71 publications

Recent Advances in Nonfullerene Acceptors for Organic Solar Cells

Recent Advances in Nonfullerene Acceptors for Organic Solar Cells

Revisiting the Optimal Nano‐Morphology: Towards Amorphous Organic Photovoltaics

Ground and Excited States of Bis‐4‐Methoxybenzyl‐Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies

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