An Organic Dyad Composed of Diathiafulvalene‐Functionalized Diketopyrrolopyrrole–Fullerene for Single‐Component High‐Efficiency Organic Solar Cells

Narayanaswamy, Krithika; Venkateswararao, A.; Nagarjuna, P.; Bishnoi, Swati; Gupta, Vinay; Chand, Suresh; Singh, Surya Prakash

doi:10.1002/anie.201602969

Cited by 62 publications

(58 citation statements)

References 61 publications

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“…However, the PV performances of SC‐OSCs are still lower than those of BHJ OSCs and most materials evaluated in SC‐OSCs led to PCE values often much below 0.5%. However, SC‐OSCs using discrete molecules such as a dithiafulvalene‐functionalized diketopyrrolopyrrole‐C 60 dyad and a triad based on an oligothiophene‐fullerene conjugate have recently led to encouraging PCEs of 2.2% and 2.4%, respectively.…”

Section: Tpa‐based Push–pull Molecular Donors For Organic Photovoltaicsmentioning

confidence: 99%

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

107

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This review article gives an overview of past and current activities in the Linear Conjugated Systems Group of Angers and in the IPOC – Functional Polymers Group of the Institute of Polymer Chemistry of Stuttgart on the use of triphenylamine (TPA) as versatile building block for organic electronics. In the first part, the properties of TPA itself are introduced including geometrical and energy level considerations. Dimerization of TPA to tetraphenylbenzidine upon electrochemical oxidation is highlighted. The blocking of TPA para‐positions and its implications in terms of electroactivity is further discussed. The second part shows that dimerization of TPA as pendant redox‐active moieties in polymers is a versatile strategy to crosslink polymer films. Coming from redox homopolymers the crosslinking strategy is extended towards conjugated redox polymers based on polythiophenes and block copolymers. Conductivity mechanisms and the influence of doping level on conductivity are probed with cyclic voltammetry coupled with in situ conductance and four‐point probe measurements. The last part is dedicated to the use of TPA as an electron‐donating block in the design of donor‐π‐acceptor chromophores and their use as active material in organic photovoltaics. An overview of some relevant TPA‐based push–pull molecules from the literature and our contribution to this field is presented emphasizing the progress of the photovoltaic performance of organic solar cells made over the last decade. © 2018 Society of Chemical Industry

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Section: Tpa‐based Push–pull Molecular Donors For Organic Photovoltaicsmentioning

confidence: 99%

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

107

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“…Menna and co-workers have reported a fulleropyrrolidine-squaraine dyad (33) (Scheme 9) and investigated its potentialities for the realization of SMOSCs for photodetection. [116] It is noteworthy that the FF value of 0.49 is much higher than for most of SMOSCs based on dyads reported so far, which suggests that the material presents good hole-transport properties. [115] Narayanaswamy et al have synthesized a dyad composed of a dithiafulvalene-functionalized bis(dithienyl)-DPP-fullerene as active material for SMOSCs (34).…”

Section: Smoscs Based On Conjugated Molecular D-a Systemsmentioning

confidence: 75%

“…[114] This problem can be circumvented by the insertion of insulating linkers between the donor and the fullerene unit, according to the BHJ model. [116] The introduction of a dithiafulvenyl group in the structure was motivated by an expected increase of donor effect and improved charge transport properties. In this regard, some recent works indicate that within certain conditions, dyads with a direct fixation of a linearly conjugated chain on C 60 can lead to materials with interesting photovoltaic properties.…”

Section: Smoscs Based On Conjugated Molecular D-a Systemsmentioning

confidence: 99%

The Dawn of Single Material Organic Solar Cells

2018

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Single material organic solar cells (SMOSCs) are based on ambivalent materials containing electron donor (D) and acceptor (A) units capable to ensure the basic functions of light absorption, exciton dissociation, and charge transport. Compared to bicomponent bulk heterojunctions, SMOSCs present several major advantages such as considerable simplification of cell fabrication and a strong stabilization of the morphology of the D/A interface, and thus of the cell lifetime. In addition to these technical issues, SMOSCs pose fundamental questions regarding the possible formation, and dissociation of excitons on the same molecular D–A architecture. SMOSCs are developed with various approaches, namely “double‐cable” polymers, block copolymers, oligomers, and molecules that differ by the donor platform: polymer or molecule, the nature of A, the D–A connection, and the intra‐ and intermolecular interactions of D and A. Although for several years the maximum efficiency of SMOSCs has remained limited to 1.0–1.5%, impressive progress has been recently accomplished leading to SMOSCs with 4.0–5.0% efficiency. Here, recent advances in the synthesis of D–A materials for SMOSCs are presented in the broader context of the chemistry of organic photovoltaic materials in order to discuss possible directions for future research.

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“…In spite of these remarkable performances, the realization of solution-processed BHJ solar cells still poses a number of problems related to both the nature of the active materials and the fabrication process [11]. For example, the finecontrol of phase separation and achieving high chargecarrier mobility in active layers are still very difficult with BHJ solar cells [ As another interesting strategy, electron donoracceptor dyad, triad, multiad and block copolymer molecules or all-in-one molecules where the electron donor (D) and acceptor (A) units are covalently linked in a single molecule have been reported for their potential as photovoltaic materials [12,[14][15][16][17][18][19]. These single-component photovoltaic materials possess multifunctions such as light harvesting, exciton dissociation and electron and hole transport.…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, several major advantages, such as a considerable simplification of device fabrication, stabilization of the morphology of the active material, and efficient (or fast) charge separation can be expected in the single-component OSCs [11]. At present, the PCE for single-component OSCs has surpassed 2% [12,15,17], which is lower than that of BHJ solar cells. This is because the design of electron donor-acceptor molecules for efficient single-component OSCs is in fact difficult.…”

Section: Introductionmentioning

confidence: 99%

Mesogenic complementary absorbing dyads based on porphyrin and perylene units

Kong

Gong

Dai

et al. 2018

J. Porphyrins Phthalocyanines

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Five novel dyads, consisting of a tetraphenylporphyrine unit connected to a perylene monoimide diester unit via a flexible bridge -CONH-(CH 2 ) n -(n = 4, 6, 8, 10 and 12), have been synthesized. Their structures were characterized by 13 C and 1 H nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry and elemental analysis. The UV-vis absorption spectra revealed these dyads have broad optical absorption in the ultraviolet and visible regions due to the complementary absorption of the two units. The differential scanning calorimetry traces and polarized optical microscopy textures showed all these dyads have columnar liquid crystal phases. Cyclic voltammetry revealed the highest occupied molecular orbitals of the dyads located on the porphyrin units, and the lowest unoccupied molecular orbitals located on the perylene units. In addition, these results were in agreement with that of the theoretical modeling. When excited at 423 or 473 nm, the photoluminescent emission spectra showed that the degree of fluorescence quenching of porphyrin units increased as the spacers became shorter. This quenching was ascribed to intramolecular photoinduced electron transfer, which also induced the dyad molecules to form the charge-separated states. The charge-separated molecules were further confirmed by the photocurrent response curves. These behaviors of broad absorption of the ultraviolet-visible light, yielding the charge-separated states of the molecules when excited and the formation of columnar liquid crystal phase made these dyads candidates for single-component photovoltaic active materials.

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An Organic Dyad Composed of Diathiafulvalene‐Functionalized Diketopyrrolopyrrole–Fullerene for Single‐Component High‐Efficiency Organic Solar Cells

Cited by 62 publications

References 61 publications

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

The Dawn of Single Material Organic Solar Cells

Mesogenic complementary absorbing dyads based on porphyrin and perylene units

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