- Dendritic-Like Molecules Built on a Pillar[5]arene Core as Hole Transporting Materials for Perovskite Solar Cells
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Multi-branched molecules have recently demonstrated interesting behaviour as charge-transporting materials within the fields of perovskite solar cells (PSCs). For this reason, extended triarylamine dendrons have been grafted onto a pillar[5]arene core to generate dendrimer-like compounds, which have been used as hole-transporting materials (HTMs) for PSCs. The performances of the solar cells containing these novel compounds have been extensively investigated. Interestingly, a positive dendritic effect has been evidenced as the hole transporting properties are improved when going from the first to the second-generation compound. The stability of the devices based on the best performing pillar[5]arene material has been also evaluated in a high-throughput ageing setup for 500 h at high temperature. When compared to reference devices prepared from spiro-OMeTAD, the behaviour is similar. An analysis of the economic advantages arising from the use of the pillar[5]arene-based material revealed however that our pillar[5]arene-based material is cheaper than the reference.
- Abate, Antonio,Bettucci, Ottavia,Cabrera-Espinoza, Andrea,Collavini, Silvia,Delgado, Juan Luis,K?bler, Hans,Matsuda, Wakana,Nierengarten, Iwona,Nierengarten, Jean-Fran?ois,Pascual, Jorge,Reginato, Gianna,Seki, Shu,Turren-Cruz, Silver-Hamill,V?lker, Sebastian F.
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p. 8110 - 8117
(2021/06/26)
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- Direct iodination of electron-deficient benzothiazoles: Rapid access to two-photon absorbing fluorophores with quadrupolar D-π-A-π-D architecture and tunable heteroaromatic core
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Direct iodination of benzothiazoles under strong oxidative/acidic conditions leads to a mixture of iodinated heteroarenes with 1-2 major components, which are easily separable and which structures depend on the I2 equivalents used. Among the unexpected bu
- Fakis, Mihalis,Georgiou, Dimitris,Hrobárik, Peter,Nociarová, Jela,Osusky, Patrik,Polyzos, Ioannis,Rakovsky, Erik
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p. 3460 - 3465
(2021/05/31)
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- Oxidative C-H Homocoupling of Push-Pull Benzothiazoles: An Atom-Economical Route to Highly Emissive Quadrupolar Arylamine-Functionalized 2,2′-Bibenzothiazoles with Enhanced Two-Photon Absorption
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Copper(II)-catalyzed C-H/C-H coupling of dipolar 2-H-benzothiazoles end-capped with triphenylamine moieties affords highly fluorescent 2,2′-bibenzothiazoles with quadrupolar (D-π-A-π-D) architecture displaying large two-photon absorption (TPA) cross sections (543-1252 GM) in the near-infrared region. The notably higher TPA performance as compared to quadrupolar π-systems with a widely used 2,2′-bipyridine core, along with the ease of the synthesis and chelating N^N ability, makes the title biheteroaryl platform an attractive building block for a large scope of functional dyes exploiting nonlinear optical phenomena.
- Fakis, Mihalis,Georgiou, Dimitris,Gyepes, Róbert,Hrobárik, Peter,Nociarová, Jela,Osusky, Patrik,Polyzos, Ioannis,Smolí?ek, Maro?
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p. 5512 - 5517
(2021/07/31)
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- Arylamino-fluorene derivatives: Optically induced electron transfer investigation, redox-controlled modulation of absorption and fluorescence
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A series of biarylaminofluorene-based systems with donor-π-donor (D-π-D) structure have been designed and synthesized in order to study the dependence on the π-conjugated bridge length of the intervalence charge-transfer transitions (IV-CT) and of the electronic coupling between the redox centers. To this purpose cyclic voltammetry, UV/Vis-NIR, fluorescence spectroscopy and computational investigations have been carried out to characterize the electronic structure of the compounds in the neutral as well as in the mono- and dication states. Additionally, a study of related D-π compounds has been performed to elucidate the effect of the interaction between two redox centers. Interestingly it was observed that the mono- and dication species exhibit intense transition bands in the NIR region, in the 10000-15000 cm?1 range, whose intensity depends on the oxidation state and thus it can be reversibly tuned by an applied potential. In a similar way, all compounds show an oxidation state dependent fluorescence which leads to electrofluorochromism. Particularly significant is the mixed valence behavior that provides these systems singular optoelectronic properties, making them excellent active components for electrochromic and electrofluorochromic applications.
- Accorsi, Gianluca,Beneduci, Amerigo,Capodilupo, Agostina-Lina,Cardone, Antonio,Corrente, Giuseppina Anna,Fabiano, Eduardo,Giannuzzi, Roberto,Gigli, Giuseppe,Manni, Francesca
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- Monocarbazole/dicarbazole hole transport material as well as preparation method and application thereof
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The invention discloses a monocarbazole/dicarbazole hole transport material as well as a preparation method and application thereof. The chemical structural general formula of the monocarbazole/dicarbazole hole transport material is shown as a formula I.
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- Luminescence Tunable Europium and Samarium Complexes: Reversible On/Off Switching and White-Light Emission
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Single-molecule functional materials with luminescence tunable by external stimuli are of increasing interest due to their application in sensors, display devices, biomarkers, and switches. Herein, new europium and samarium complexes with ligands having triphenylamine (TPA) groups as the redox center and 2,2′-bipyridine (bpy) as the coordinating groups and diketonate (tta) as the second ligand have been constructed. The complexes show white-light emission in selected solvents for proper mixtures of the emission from Ln3+ ions and the ligands. Meanwhile, they exhibit reversible luminescence switching on/off properties by controlling the external potential owing to intramolecular energy transfer from the Ln3+ ions to the electrochemically generated radical cation of TPA+. Time-dependent density functional theory (TD-DFT) calculations have been performed to study the electronic spectra. The proposed intramolecular energy transfer processes have been verified by density functional theory (DFT) studies.
- Chen, Jing,Xie, Ziyu,Meng, Lingyi,Hu, Ziying,Kuang, Xiaofei,Xie, Yiming,Lu, Can-Zhong
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p. 6963 - 6977
(2020/05/18)
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- Influence of Donor-Substituents on Triphenylamine Chromophores Bearing Pyridine Fragments
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Efficient synthetic routes that combine different palladium-catalyzed cross-coupling reactions have been developed for the preparation of a new family of push-pull derivatives in which pyridine was used as the acceptor group and different para-substituted diphenylamines as the donor groups. All compounds showed absorption in the UV/Vis region and blue-green emission with high quantum yields. Significant red shifts were observed in the absorption and fluorescence emission maxima on increasing the electron-donating ability of the substituents or on incorporating a π-conjugated linker. This finding can be explained on the basis of enhanced intramolecular charge transfer (ICT). Strong emission solvatochromism confirmed the formation of an intramolecular charge-separated emitting state. The HOMO-LUMO energy gaps have been estimated by experimental electrochemical measurements and the results were interpreted with the aid of DFT calculations. The thermal behavior of all materials has also been studied by differential scanning calorimetry.
- Tydlitát, Ji?í,Fecková, Michaela,le Poul, Pascal,Pytela, Old?ich,Klikar, Milan,Rodríguez-López, Julián,Robin-le Guen, Fran?oise,Achelle, Sylvain
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p. 1921 - 1930
(2019/02/25)
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- ORGANIC DYES, COMPOSITIONS AND DYE-SENSITIZED SOLAR CELL
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The present invention relates to an organic dye having improved stability to heat, light and water, to a composition comprising the same, and to a dye-sensitized solar cell and, more specifically, to an organic dye represented by chemical formula 1, to a composition comprising the same, and to a dye-sensitized solar cell. The chemical formula 1 is the same as defined in claim 1.COPYRIGHT KIPO 2020
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Paragraph 0095-0096
(2019/12/25)
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- Effect of alkyl chain length on the properties of triphenylamine-based hole transport materials and their performance in perovskite solar cells
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A new series of diacetylide-triphenylamine (DATPA) derivatives with five different alkyl chains in the para position, MeO, EtO, nPrO, iPrO and BuO, were synthesised, fully characterised and their function as hole-transport materials in perovskite solar cells (PSC) studied. Their thermal, optical and electrochemical properties were investigated along with their molecular packing and charge transport properties to analyse the influence of different alkyl chains in the solar cell parameters. The shorter alkyl chain facilitates more compact packing structures which enhanced the hole mobilities and reduced recombination. This work suggests that the molecule with the methoxy substituent (MeO) exhibits the best semiconductive properties with a power conversion efficiency of up to 5.63%, an open circuit voltage (Voc) of 0.83 V, a photocurrent density (Jsc) of 10.84 mA cm-2 and a fill factor of 62.3% in perovskite solar cells. Upon replacing the methoxy group with longer alkyl chain substituents without changing the energy levels, there is a decrease in the charge mobility as well as PCE (e.g. 3.29% for BuO-DATPA). The alkyl chain length of semiconductive molecules plays an important role in achieving high performance perovskite solar cells.
- Fuentes Pineda, Rosinda,Troughton, Joel,Planells, Miquel,Sanchez-Molina Santos, Irene,Muhith, Farmin,Nichol, Gary S.,Haque, Saif,Watson, Trystan,Robertson, Neil
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p. 1252 - 1260
(2018/01/17)
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- Panchromatic Push-Pull Dyes of Elongated Form from Triphenylamine, Diketopyrrolopyrrole, and Tetracyanobutadiene Modules
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Several symmetrical and unsymmetrical thiophene-functionalized diketopyrrolopyrrole chromophores bearing a bis(p-methoxyphenyl)-p-phenylamine substituent were synthesized through palladium-catalyzed cross-coupling reactions. Mono-substitution and di-substitution occur using either alkyne or borolane groups, allowing the preparation of mixed systems. The alkyne derivatives could be prepared in high yields, and are versatile building blocks for the [2+2] cyAcloaddition of tetracyanoethylene, leading to 1,1,4,4-tetracyanobuta-1,3-diene derivatives. These interesting push-pull molecules exhibit a rich redox activity, which is understandable in light of the behavior of appropriate reference compounds. These innovative and rationally designed scaffolds are highly colored, exhibiting high absorption coefficients and spanning an absorption range of more than 600A nm of the UV/Vis electromagnetic spectrum.
- Heyer, Elodie,Ziessel, Raymond
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p. 2109 - 2116
(2015/09/15)
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- Charge transfer emission in oligotriarylamine-triarylborane compounds
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Donor-acceptor compounds exhibiting charge transfer emission are of interest in a variety of different contexts, for example, for nonlinear optical processes and for sensor applications. Recently investigated triarylamine-triarylborane compounds represent an important class of donor-acceptor systems, and we explored to what extent their charge-transfer properties can be further improved by using stronger amine donors and borane acceptors than prior studies. The oligotriarylamine employed here is a much stronger donor than previously used triarylamines containing single nitrogen centers. In order to increase the acceptor strength, the electron-accepting unit was equipped with two (instead of one) dimesitylboron substituents. In our comparative study, six donor-acceptor compounds were synthesized and investigated by cyclic voltammetry and optical spectroscopy. An increase of the donor strength through replacement of an ordinary triarylamine by an oligotriarylamine unit leads to the expected energetic stabilization of charge transfer (CT) excited states, but the emission solvatochromism is not more pronounced. The attempted increase of the acceptor strength by substitution of the acceptor moiety by two (instead of one) dimesitylboron groups leads to a drastic decrease of emission quantum yields. On the basis of these results, our purely experimental study provides fundamental guidelines for the design of new triarylamine-triarylborane donor-acceptor compounds with favorable charge-transfer emission properties.
- Bonn, Annabell G.,Wenger, Oliver S.
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p. 4097 - 4107
(2015/05/05)
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- Fluoride binding to an organoboron wire controls photoinduced electron transfer
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We demonstrate that the rates for long-range electron transfer can be controlled actively by tight anion binding to a rigid rod-like molecular bridge. Electron transfer from a triarylamine donor to a photoexcited Ru(bpy)32+ acceptor (bpy = 2,2′-bipyridine) across a 2,5-diboryl-1,4-phenylene bridge occurs within less than 10 ns in CH2Cl2 at 22 °C. Fluoride anions bind with high affinity to the organoboron bridge due to strong Lewis base/Lewis acid interactions, and this alters the electronic structure of the bridge drastically. Consequently, a large tunneling barrier is imposed on photoinduced electron transfer from the triarylamine to the Ru(bpy)32+ complex and hence this process occurs more than two orders of magnitude more slowly, despite the fact that its driving force is essentially unaffected by fluoride addition. Electron transfer rates in proteins could potentially be regulated via a similar fundamental principle, because interactions between charged amino acid side chains and counter-ions can modulate electronic couplings between distant redox partners. In artificial donor-bridge-acceptor compounds, external stimuli have been employed frequently to control electron transfer rates, but the approach of exploiting strong Lewis acid/Lewis base interactions to regulate the tunneling barrier height imposed by a rigid rod-like molecular bridge is conceptually novel and broadly applicable, because it is largely independent of the donor and the acceptor, and because the effect is not based on a change of the driving-force for electron transfer. The principle demonstrated here can potentially be used to switch between conducting and insulating states of molecular wires between electrodes. This journal is
- Chen, Jing,Wenger, Oliver S.
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p. 3582 - 3592
(2015/05/27)
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- Diacetylene bridged triphenylamines as hole transport materials for solid state dye sensitized solar cells
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We have synthesized and characterized a series of triphenylamine-based hole-transport materials (HTMs), and studied their function in solid-state dye sensitized solar cells (ss-DSSCs). By increasing the electron-donating strength of functional groups (-H -Me -SMe -OMe) we have systematically shifted the oxidation potential and ensuing photocurrent generation and open-circuit voltage of the solar cells. Correlating the electronic properties of the HTM to the device operation highlights a significant energy offset required between the Dye-HTM highest occupied molecular orbital (HOMO) energy levels. From this study, it is apparent that precise control and tuning of the oxidation potential is a necessity, and usually not achieved with most HTMs developed to date for ss-DSSCs. To significantly increase the efficiency of solid-state DSSCs understanding these properties, and implementing dye-HTM combinations to minimize the required HOMO offset is of central importance.
- Planells, Miquel,Abate, Antonio,Hollman, Derek J.,Stranks, Samuel D.,Bharti, Vishal,Gaur, Jitender,Mohanty, Dibyajyoti,Chand, Suresh,Snaith, Henry J.,Robertson, Neil
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p. 6949 - 6960
(2013/07/26)
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- Charge transfer through cross-hyperconjugated versus cross-π-conjugated bridges: An intervalence charge transfer study
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Recently there has been much interest in electron transfer and transport through cross-conjugated molecules as interesting test cases for the interplay between molecular and electronic structure as well as potential motifs in the design of new compounds f
- Goeransson, Erik,Emanuelsson, Rikard,Jorner, Kjell,Markle, Todd F.,Hammarstroem, Leif,Ottosson, Henrik
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p. 3522 - 3532
(2013/11/19)
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- Tunable, strongly-donating perylene photosensitizers for dye-sensitized solar cells
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Broadly absorbing perylene dyes bearing three-triarylamine groups were synthesized via Sonogashira coupling. The triarylamine moieties allowed further installation of electron donating ability, to enable tuning of the oxidation potential and optical band gap. With introducing more electron-donating groups into the three-triarylamine moieties the device performance was improved. The trend can be rationalized by the distribution of the electron density in the HOMO of the perylene moiety as well as the light-harvesting property of the perylene dyes.
- Mathew, Simon,Imahori, Hiroshi
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experimental part
p. 7166 - 7174
(2012/01/13)
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- Structure-property relationships in conjugated donor-acceptor molecules based on cyanoanthracene: Computational and experimental studies
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Two series of π-conjugated bipolar compounds, namely, 9-phenyl-10-anthronitriles (PAN series) and 9-phenylethynyl-10-anthronitriles (PEAN series), having inherent redox centers have been synthesized and their electronic absorption, fluorescence emission,
- Lin, Jui-Hsien,Elangovan, Arumugasamy,Ho, Tong-Ing
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p. 7397 - 7407
(2007/10/03)
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- Synthesis, (non)linear optical and redox properties of a donor- substituted truxenone derivative
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A two-dimensional NLO chromophore (7) with three donor-substituted branches and truxenone as the central coupling unit was synthesised from tribromotruxenone by Stille coupling with N,N-di(4-methoxyphenyl)- 4'(tributylstannylethynyl)phenylamine. UV/visibl
- Lambert, Christoph,Noell, Gilbert,Schmaelzlin, Elmar,Meerholz, Klaus,Braeuchle, Christoph
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p. 2129 - 2135
(2007/10/03)
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