Organic dyes containing dithieno[2,3-d:2′,3′-d′]thieno[3,2-b:3′,2′-b′]dipyrrole core for efficient dye-sensitized solar cells

Wang, Zhihui; Liang, Mao; Tan, Yulin; Ouyang, Liyan; Sun, Zhe; Xue, Song

doi:10.1039/c4ta06705c

Cited by 54 publications

(31 citation statements)

References 62 publications

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“…Some molecules containing the pyrrole moiety find application also as therapeutic compounds like fungicides, antibiotics, anti‐inflammatory drugs, cholesterol reducing drugs, and antitumor agents . Pyrrole has been used in technological applications like, for example, polymers with remarkable electric conductivity and in dye‐sensitized solar cells …”

Section: Introductionmentioning

confidence: 99%

New atomistic model of pyrrole with improved liquid state properties and structure

Macchiagodena

Mancini

Pagliai

et al. 2017

Int J of Quantum Chemistry

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Structural characterization of liquid pyrrole has been obtained by performing classical molecular dynamics simulations with a new parameterization of electrostatic interactions. Despite the relatively simple molecular structure of pyrrole, a correct and accurate representation of its intermolecular interactions in bulk phase is a challenging task, since these are affected at short range by the quadrupole-quadrupole term. This new parameterization permits not only to correctly describe the liquid structure but also to obtain macroscopic properties in excellent agreement with experiments.bulk properties, force field, molecular dynamics, quadrupole moment 1 | I N TR ODU C TI ON Pyrrole (C 4 H 5 N) is one of the simplest and most representative heteroaromatic molecules. Its five-membered ring is the building block of several molecules of biological and pharmacological relevance, such as amino acids, indole alkaloids, [1] and porphyrins. [2] Some molecules containing the pyrrole moiety find application also as therapeutic compounds like fungicides, antibiotics, anti-inflammatory drugs, [3] cholesterol reducing drugs, [4] and antitumor agents. [5] Pyrrole has been used in technological applications like, for example, polymers with remarkable electric conductivity [6] and in dye-sensitized solar cells. [7,8] The structure of pyrrole (see Figure 1) features an NAH group and a p system, which permit effective self-aggregation into clusters through the formation of a weak NAHÁ Á Á p hydrogen bonds. This behavior has been confirmed by experimental and theoretical studies which have shown the tendency to form T-shaped aggregates, [9][10][11][12][13] which are typical structures found in the so called "quadrupolar crystals". In particular, it has been observed in microwave spectroscopy experiments [14] that the angle formed by two monomers approaches to $55 with a distance between the centers of mass of $4:1 Å.The nature of the NAHÁ Á Á p hydrogen bond and the relevance of high multipole contributions to the liquid structure are not yet completely understood, especially in the liquid state. In fact, although several studies about small clusters are available, only few experimental and theoretical studies have been performed on liquid pyrrole. [13,[15][16][17] Hence, in this work, we present a computational study on liquid pyrrole with the purpose of accurately determining its structural features and bulk properties.The structure of liquid pyrrole and its evolution over time has been described by classical molecular dynamics (MD), which allows to estimate macroscopic properties from microscopic models. To obtain results comparable with experiments, it is mandatory to employ an accurate force field (FF), which describes the interactions at atomic and molecular level using a set of functional forms based on a limited number of parameters. Some properties are very sensitive to the electrostatic part of the force field, which in the most widely used FFs is described using partial atomic charges.Int J Quantum Chem. 2018;118:e25554.

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Section: Introductionmentioning

confidence: 99%

New atomistic model of pyrrole with improved liquid state properties and structure

Macchiagodena

Mancini

Pagliai

et al. 2017

Int J of Quantum Chemistry

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“…It is the key to the photoactivation of the phytochrome enzyme 12 . Pyrrole is also a basic building block in many biologically and technologically important systems, such as polyamide DNA-binding agents in chemical biology 13 14 , dye-sensitized solar cells 15 16 , the polypyrrole conducting polymer 17 and self-assembled architectures containing donor–acceptor units 18 . Moreover, it is a prototypical heteroaromatic molecule that undergoes highly efficient non-radiative relaxation on a πσ * potential surface 19 20 21 .…”

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confidence: 99%

Identification of a new electron-transfer relaxation pathway in photoexcited pyrrole dimers

et al. 2016

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Photoinduced electron transfer is central to many biological processes and technological applications, such as the harvesting of solar energy and molecular electronics. The electron donor and acceptor units involved in electron transfer are often held in place by covalent bonds, π–π interactions or hydrogen bonds. Here, using time-resolved photoelectron spectroscopy and ab initio calculations, we reveal the existence of a new, low-energy, photoinduced electron-transfer mechanism in molecules held together by an NH⋯π bond. Specifically, we capture the electron-transfer process in a pyrrole dimer, from the excited π-system of the donor pyrrole to a Rydberg orbital localized on the N-atom of the acceptor pyrrole, mediated by an N–H stretch on the acceptor molecule. The resulting charge-transfer state is surprisingly long lived and leads to efficient electronic relaxation. We propose that this relaxation pathway plays an important role in biological and technological systems containing the pyrrole building block.

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“…43 Because of their strong absorption in the visible to near-infrared region, they also participate as light absorber together with perovskite in the low energy region. 44 By using smaller DCV-substituted S,N-heteropentacenes higher PCEs of up to 6.5% were obtained in vacuum-processed and up to 4.9% in solution processed organic solar cells. 44 By using smaller DCV-substituted S,N-heteropentacenes higher PCEs of up to 6.5% were obtained in vacuum-processed and up to 4.9% in solution processed organic solar cells.…”

Section: Several Low Band Gap Polymeric Semiconductors Have Also Beenmentioning

confidence: 99%

A–D–A-type S,N-heteropentacene-based hole transport materials for dopant-free perovskite solar cells

et al. 2015

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This work reports the design and synthesis of acceptor-donor-acceptor (A-D-A) type low band gap hole transport materials (HTM) comprising S,N-heteropentacene central units for solid-state perovskite-based solar cells. The optical and electrochemical properties were tuned by the insertion of thiophene or ethylenedioxythiophene units in the molecular backbone. These HTMs showed strong absorption in the visible region and suitable highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies with respect to the CH3NH3PbI3 perovskite. Mesoscopic solid state perovskite solar cells prepared by solution-2 processing using these HTMs generated power conversion efficiencies (PCE) of 10.3-11.4% without the use of any additive or dopant. The charge transfer behavior between photoexcited perovskite and the HTMs was further investigated by photo-induced absorption spectroscopy. Introduction Recently, organometal halide CH3NH3PbX3 (X = Cl, Br, I) perovskites 1, 2 have received considerable attention in solid-state photovoltaics due to their several interesting features, such as intense light absorption across the visible spectrum, high charge carrier mobilities, direct band gap, longer carrier diffusion length, and small exciton binding energy. 3-8 Miyasaka and coworkers were the first to report the incorporation of CH3NH3PbX3 (X = Br, I) perovskite as sensitizer in liquid electrolyte-based dye-sensitized solar cells reaching power conversion efficiencies (PCE) of 3.8%. 9 Later, Park et al. reported efficient and stable solid-state CH3NH3PbI3based perovskite solar cells with PCEs as high as 9.7%. 3 Since then, by extensive optimization of the metal oxide scaffolds and device processing conditions PCEs have been improved to over 19% using state of the art 2,2',7,7'-tetrakis(N,N-di-p-methoxyphenylamino)-9,9'-spirobifluorene (spiro-MeOTAD) as hole transporting material. 10-12 Seok and co-workers reported a series of spiro-MeOTAD derivatives showing an enhanced PCE of 16.7% for the o-OMe substituted derivatives compared to the conventional p-OMe counterpart. 13 However, due to low hole mobility and conductivity of spiro-MeOTAD in the pristine form, additives, such as Lithium bis(trifluoromethanesulfonyl)imide (Li-TFSI) 14 and cobalt complexes as p-type dopants, 15 are necessary to improve the device performance. Although PCEs up to 12.8% were reported for HTM-free perovskite devices, 16-19 the most efficient solar cells usually employed organic HTMs which play a key role for the hole transport and reduce charge recombination processes. 20 In this respect, a wide range of material classes consisting of pyrene, 21 thiophene, 22,Heteropentacene-based A-D-A type hole transport materials with suitable frontier orbital energy levels were synthesized and implemented in perovskite-based solar cells generating promising power conversion efficiencies up to 11.4%. Table of ContentHeteropentacene-based A-D-A type hole transport materials with suitable frontier orbital energy levels were synthesized and impl...

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Organic dyes containing dithieno[2,3-d:2′,3′-d′]thieno[3,2-b:3′,2′-b′]dipyrrole core for efficient dye-sensitized solar cells

Abstract: We report two new triarylamine-cyanoacrylic acid based push–pull dyes, X76 and X77, featuring the π-conjugated linkers of dihexyl- and dihexyloxybenzene-substituted dithieno[2,3-d:2′,3′-d′]thieno[3,2-b:3′,2′-b′]dipyrrole (DTDP), respectively.

Cited by 54 publications

References 62 publications

New atomistic model of pyrrole with improved liquid state properties and structure

New atomistic model of pyrrole with improved liquid state properties and structure

Identification of a new electron-transfer relaxation pathway in photoexcited pyrrole dimers

A–D–A-type S,N-heteropentacene-based hole transport materials for dopant-free perovskite solar cells

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