High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

• Paul B. Geraghty,
• Calvin Lee,
• Jegadesan Subbiah,
• Wallace W. H. Wong,
• James L. Banal,
• Mohammed A. Jameel,
• Trevor A. Smith and
• David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

• devices with PTB7-Th resulting in high-performance OPV devices with up to 10.7% PCE. Keywords: molecular materials; nematic liquid crystal; organic solar cells; organic synthesis; p-type organic semiconductors; small molecule; Introduction Bulk heterojunction (BHJ) organic solar cells (OSC), a blend of

• chromophores can be accessed, and thereby the thermal stability of OPV devices containing these new materials can be improved. We are currently examining BQR in printed solar cells. In all cases in our structure–property relationship studies, devices incorporating materials that exhibited a high temperature

• characteristics of BXR:PC71BM BHJ solar cells. (a) device structure, (b) J–V curves for as-cast, (c) J–V curves for SVA with THF, (d) and J–V curves for TA at 120 °C for 10 min. J–V characteristics of BTxR:PC71BM ternary BHJ solar cells, a) device architecture, and b) J–V curve for BTxR containing devices. J–V

Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

• Dominik Urselmann,
• Konstantin Deilhof,
• Bernhard Mayer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2016, 12, 2055–2064, doi:10.3762/bjoc.12.194

• -transfer characteristics [59][60][61][62][63], as hole-transport materials [64], for applications in mesoporous organo silica hybrid materials [65], and as chromophores in dye-sensitized solar cells [66][67][68]. Furthermore, (oligo)phenothiazines in their native reduced forms display a pronounced ability

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• reduction potentials (more positive), allowed for air-stable fabrication of organic field effect transistors (OFETs), and showed promise in solar cells [13][32]. Some homoleptic metal complexes, such as Ir(III) phenylpyridine-based complexes, are favored for their use in light-emitting devices and the

• : calcd for C96H56F4N6Zn, 1633.37; found, 1629.75; anal. calcd for: C, 73.46; H, 3.45; N, 5.14; found: C, 73.42; H, 3.69; N, 5.06. Organic solar cells Photovoltaic properties were studied using the inverted configuration: ITO/ZnO/P3HT:Acceptor/MoO3/Ag. ITO-coated glass (R = 15 Ω/sq) substrates were

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• use in organic solar cells. In this paper, four 4,8-bis(5-alkyl-2-thienyl)benzo[1,2-b:4,5-b′]dithiophene (TBDT)-containing A–π–D–π–A-type small molecules (COOP-nHT-TBDT, n = 1, 2, 3, 4), having 2-cyano-3-octyloxy-3-oxo-1-propenyl (COOP) as terminal group and regioregular oligo(3-hexylthiophene) (nHT

• levels increased (from −5.68 to −5.34 eV) with the increase of the length of the π-conjugated bridge. Organic solar cells using the synthesized compounds as the electron donor and PC61BM as the electron acceptor were fabricated and tested. Results showed that compounds with longer oligothiophene π

• ; benzodithiophene; π-bridge; chain length effect; organic solar cell; Introduction Solution-processed organic solar cells (OSCs) are considered to be one of the most promising renewable energy technologies because of the advantages of low cost, lightweight, flexibility, and great potentials in large-scale

Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

• Desta Gedefaw,
• Marta Tessarolo,
• Margherita Bolognesi,
• Mario Prosa,
• Renee Kroon,
• Wenliu Zhuang,
• Patrik Henriksson,
• Kim Bini,
• Ergang Wang,
• Michele Muccini,
• Mirko Seri and
• Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

• heterojunction solar cells. Even though PTzBDT-1 showed favourable optical and electrochemical properties, the devices based on this polymer present a power conversion efficiency of 3.3%, considerably lower than the efficiency of 4.7% obtained for the analogous solar cells based on PTzBDT-2. The lower

• performance is presumably attributed to the limited solubility of the PTzBDT-1 in organic solvents resulting in enhanced aggregation and poor intermixing with the acceptor material in the active layer. Keywords: alkyl side chains; benzodithiophene; bulk heterojunction solar cells; 2D conjugated polymers

• ; fluorinated benzotriazole; Introduction Over the past decades the research on bulk heterojunction (BHJ) polymer solar cells (PSCs) has been intensified due to the attractive perspectives of producing lightweight and flexible devices via a scalable printing technology at low-cost. The active layer consists of

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• synthesized. Based on density functional theory calculations, the star-shaped TTA-DPP4 has a larger oscillator strength than the linear TTA-DPP2, and consequently, better photoabsorption property over a wide range of visible wavelengths. The photovoltaic properties of organic solar cells based on TTA-DPP4 and

• (40–60 nm). Keywords: bulk heterojunction; diketopyrrolopyrrole; organic solar cells; star-shaped oligomers; tetrathienoanthracene; Introduction Solution-processable organic semiconductors have been intensively studied as key materials for low-cost, flexible, and large-area optoelectronic devices

• , including organic solar cells (OSCs) [1][2][3][4]. OSCs have drawn much attention as promising next-generation renewable energy sources because abundant sun-light energy can be directly converted into electricity. Recently, the power conversion efficiencies (PCEs) of OSCs based on small molecules with bulk

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

• Wei Li,
• Munechika Otsuka,
• Takehito Kato,
• Yang Wang,
• Takehiko Mori and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

• College, 771 Nakakuki, Oyama, Tochigi 323-0806, Japan 10.3762/bjoc.12.134 Abstract The ever increasing demand for clean energy has encouraged researchers to intensively investigate environmentally friendly photovoltaic devices. Inorganic–organic hybrid perovskite solar cells (PSCs) are very promising due

• ; hole transport; perovskite solar cell; polycondensation; Introduction Inorganic–organic hybrid perovskite solar cells (PSCs) have recently received significant attention due to their remarkably high power convention efficiencies (PCEs). After the seminal study reported by Miyasaka et al. in 2009 with

• the PCE of 4% [1], some key improvements have been made in designing device structures and fabrication methods, and the PCE of the PSCs rapidly increased to >20% [2][3][4][5]. Compared to the conventional organic photovoltaics and dye-sensitized solar cells (DSSCs), PSCs benefit from a broad light

Separation and identification of indene–C₇₀ bisadduct isomers

• Bolong Zhang,
• Jegadesan Subbiah,
• David J. Jones and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2016, 12, 903–911, doi:10.3762/bjoc.12.88

• separation; electron acceptor; fullerene bisadduct; organic solar cell; regioisomers; Introduction Organic solar cells (OSCs) are an emerging renewable energy technology that has achieved remarkable progress over the past two decades. Compared to traditional inorganic semiconductor solar cells, OSCs promise

• a number of advantages, such as lightweight flexible devices and low-cost fabrication using roll-to-roll printing [1]. Bulk-heterojunction organic solar cells (BHJ OSC) are a specific type of OSCs which contain a blend of organic electron donor and acceptor materials as the photoactive component

• thin film nanostructure are key factors in determining the performance of these fullerene derivatives in BHJ solar cell devices. With the observations in this study, it can be argued that the success of IC70BA (and in extension, IC60BA) as the electron acceptor component in BHJ solar cells is

Indenopyrans – synthesis and photoluminescence properties

• Andreea Petronela Diac,
• Ana-Maria Ţepeş,
• Albert Soran,
• Ion Grosu,
• Anamaria Terec,
• Jean Roncali and
• Elena Bogdan

Beilstein J. Org. Chem. 2016, 12, 825–834, doi:10.3762/bjoc.12.81

• chromophores are valuable candidates for the fabrication of OLEDs [21][22], dye lasers [23], sensors [24], dye-sensitized solar cells, fluorescent probes [25] or logic gates [26]. Recently [27], 6-CF3-2H-pyran-2-ones have been reported as potential building blocks for the preparation of novel

Creating molecular macrocycles for anion recognition

• Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

• the creation and understanding of metal polypyridyl dyes [2] designed for use in solar cells [3]. I loved being in the laboratory doing research and I continued this work through my Ph.D. From Keith I learned the importance of designing function into molecules and exploiting them in a homologous

Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp²)–H bond arylations

• Fatiha Abdelmalek,
• Fazia Derridj,
• Safia Djebbar,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2015, 11, 2012–2020, doi:10.3762/bjoc.11.218

• regioselective activation of C(sp2)–H bonds. Keywords: catalysis; C–H bond arylations; desulfitative; fluorine; palladium; Introduction Fluorinated π-conjugated oligomers increasingly receive recent interest owing to their particular applications as electronic devices (e.g., in organic solar cells) [1][2][3][4

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• in organic field effect transistors and solar cells. Keywords: donor; oligothiophene; organic electronics; polythiophene; semiconductor; tetrathiafulvalene; Introduction Sulfur-rich π-functional systems are important building blocks in materials chemistry. Among them, tetrathiafulvalene (TTF

• studied polythiophene materials for organic electronics are regioregular poly(3-hexylthiophene) (P3HT) [2][3] and poly(3,4-ethylenedioxythiophene) (PEDOT) [4], which is highly conductive in its doped state. P3HT has become a benchmark polymer semiconductor for both bulk hetero-junction solar cells (BHJSCs

An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

• Sundaravel Vivek Kumar,
• Shanmugam Muthusubramanian,
• J. Carlos Menéndez and
• Subbu Perumal

Beilstein J. Org. Chem. 2015, 11, 1707–1712, doi:10.3762/bjoc.11.185

• -aminothiophenes have potential applications in the field of functional materials such as liquid crystals [13], nonlinear optical materials (NLOs) [14], organic solar cells [15], photonic polymers [16] and electroluminescent materials [17]. Nitrothiophenes are also important as chemotherapeutic agents and in a few

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• attention of chemists and physicists on high electrical conductivity and superconductivity with high Tc temperature. Recently, however, TTF and its derivatives are frequently employed as a redox-active moiety for organic electronic devices such as field-effect-transistors (FET), dye-sensitized solar cells

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• chemical means. The synthesized products can find a wide range of applications such as drug/gene delivery systems, flame retardant materials, conducting polymers, controlled release systems, diagnostic agents, and polymeric electrolytes for nano-crystalline solar cells. Curcumin (37) was converted to a

A hybrid electron donor comprising cyclopentadithiophene and dithiafulvenyl for dye-sensitized solar cells

• Gleb Sorohhov,
• Chenyi Yi,
• Michael Grätzel,
• Silvio Decurtins and
• Shi-Xia Liu

Beilstein J. Org. Chem. 2015, 11, 1052–1059, doi:10.3762/bjoc.11.118

• HOMO–LUMO gap. In turn, the direct linkage of D and A units leads to an effective π-conjugation, thus substantially lowering the HOMO–LUMO gap. Moreover, the application in dye-sensitized solar cells was investigated, showing that the power conversion efficiency increases by the insertion of the phenyl

• unit. Keywords: donor–acceptor systems; dye-sensitized solar cells; electrochemistry; intramolecular charge transfer; Knoevenagel reaction; tetrathiafulvalene; Introduction Dye-sensitized solar cells (DSSCs) have been intensively investigated as an alternative to silicon-based solar cells [1][2][3][4

• ][8] have been used in the construction of photosensitizers. Not surprisingly, tetrathiafulvalene (TTF), as a strong π-electron donor, has been incorporated into different D–π–A systems for numerous potential applications [9][10][11][12][13][14]. However, TTF-sensitized solar cells have rarely been

A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles

• Roman A. Irgashev,
• Arseny A. Karmatsky,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2015, 11, 1000–1007, doi:10.3762/bjoc.11.112

• compounds which can be applied in organic optoelectronic materials. Indeed, we have recently reported the synthesis of novel push–pull dyes IK-1,2 based on the thieno[2,3-b]indole ring system, as a donating part of dye-sensitized solar cells [8] (Figure 1). It should be noted that thieno[2,3-b]pyrrole and

• analogues. This two-step approach provides an easy access to compounds of the family of electron-rich thieno[2,3-b]indoles, which are regarded as promising building-blocks for the development of new photo- and electrosensitive molecules, e.g., novel push–pull dyes for dye-sensitized solar cells

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• -diaza-s-indacene (BODIPY) units attached by thiophene rings have been synthesised having high molar extinction coefficients. These triads were characterised and used as donor materials in small molecule, solution processable organic solar cells. Both triads were blended with PC71BM as an acceptor in

• the triads, theoretical DFT and TDDFT calculations were performed. Keywords: BODIPY; diketopyrrolopyrrole; organic semiconductors; organic solar cells; thiophene; Introduction The discovery of photoinduced electron transfer from conjugated polymers to fullerene (C60), and the favourable

• ., who have reported solar cells incorporating a hybrid thiophene–benzothiadiazole–thiophene–BODIPY derivative with power conversion efficiencies of ca. 1.25% [55]. Whilst the open circuit voltage of our best device was higher than theirs (0.62 V), in Ziessel’s work the fill factor (35%) and short

Chemistry of polyhalogenated nitrobutadienes, 14: Efficient synthesis of functionalized (Z)-2-allylidenethiazolidin-4-ones

• Viktor A. Zapol’skii,
• Jan C. Namyslo,
• Mimoza Gjikaj and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2014, 10, 1638–1644, doi:10.3762/bjoc.10.170

• efficiency as donor compound in solar cells [34]. Very recently, thiazolidinones became a target in the field of photonics and optoelectronics, potentially applicable for reversible optical data storage, photo switching of optical elements, photochromic polymers, and similar applications [35]. The background

Novel indolin-2-one-substituted methanofullerenes bearing long n-alkyl chains: synthesis and application in bulk-heterojunction solar cells

• Irina P. Romanova,
• Andrei V. Bogdanov,
• Inessa A. Izdelieva,
• Vasily A. Trukhanov,
• Gulnara R. Shaikhutdinova,
• Dmitry G. Yakhvarov,
• Shamil K. Latypov,
• Vladimir F. Mironov,
• Vladimir A. Dyakov,
• Ilya V. Golovnin,
• Dmitry Yu. Paraschuk and
• Oleg G. Sinyashin

Beilstein J. Org. Chem. 2014, 10, 1121–1128, doi:10.3762/bjoc.10.111

• methanofullerenes (AIMs) is described. Optical absorption, electrochemical properties and solubility of AIMs were studied. Poly(3-hexylthiophene-2,5-diyl) (P3HT)/AIMs solar cells were fabricated and the effect of the AIM alkyl chain length and the P3HT:AIM ratio on the solar cell performance was studied. The power

• of low-cost and flexible solar cells [1][2][3]. Organic solar cells are mainly based on bulk heterojunctions composed of a polymer donor and a fullerene acceptor. A number of promising donor materials has been developed, whereas very few successful fullerene derivatives have been proposed. The most

• plastic solar cells (PSCs) were fabricated on the P3HT/HBIM blends, the power conversion efficiency (PCE) was about 2% [8]. The P3HT/HBIM devices showed the same open-circuit voltage (Voc) as the P3HT:PCBM ones, but the short-circuit current (Jsc) and the fill factor (FF) were considerably less. It was

On the mechanism of photocatalytic reactions with eosin Y

• Michal Majek,
• Fabiana Filace and
• Axel Jacobi von Wangelin

Beilstein J. Org. Chem. 2014, 10, 981–989, doi:10.3762/bjoc.10.97

• answers to the distinction between photocatalytic and radical chain mechanisms can be derived directly from Φ. A quantification of the photon flux is rather problematic. Recently, devices became available which use solar cells for the direct measurement of photon fluxes [33]. However, chemical actinometry

First synthesis of meso-substituted pyrrolo[1,2-a]quinoxalinoporphyrins

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2014, 10, 808–813, doi:10.3762/bjoc.10.76

• ][12][13], organic light emitting diodes [14][15], near infrared dyes [16][17][18], hybrid solar cells [19][20][21][22], and biosensors [23][24][25] due to their intense optical absorptions and photoluminescence characteristics. On the other hand, compounds containing a pyrrolo[1,2-a]quinoxaline

Triphenylene discotic liquid crystal trimers synthesized by Co₂(CO)₈-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition

• Bin Han,
• Ping Hu,
• Bi-Qin Wang,
• Carl Redshaw and
• Ke-Qing Zhao

Beilstein J. Org. Chem. 2013, 9, 2852–2861, doi:10.3762/bjoc.9.321

• ][17], and organic photovoltaic solar cells (OPVs) [18][19][20]. The reported DLC oligomers [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50] are limited compared with the low-molar-mass DLCs and polymeric DLC materials, due to the

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

• Helga Seyler,
• Jegadesan Subbiah,
• David J. Jones,
• Andrew B. Holmes and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

• : conjugated polymers; continuous-flow synthesis; controlled polymerization; flow chemistry; organic solar cell materials; Introduction Poly(3-hexylthiophene), P3HT, is the most investigated material in bulk heterojunction (BHJ) organic solar cells (OSC) [1]. The reasons for its dominance in the field include

• variations to this general method [6][7][8][9]. Significant quantities of materials are required for the optimization of large-area roll-to-roll printed organic solar cells [3][10]. While some of the organic semiconducting materials can be obtained commercially an a hundreds-of-grams scale, it is important

• catalyst stock solution, afforded lower-molecular-weight polymers (Table 3, entries 2 and 3). In order to assess the device performance of P3HT synthesized using flow methods described in this study, bulk heterojunction (BHJ) solar cells were fabricated and tested. BHJ devices were fabricated with the

Structures of the reaction products of the AZADO radical with TCNQF₄ or thiourea

• Hideto Suzuki,
• Yuta Kawahara,
• Hiroki Akutsu,
• Jun-ichi Yamada and
• Shin’ichi Nakatsuji

Beilstein J. Org. Chem. 2013, 9, 1487–1491, doi:10.3762/bjoc.9.169

• clarified to play a significant role as an efficient mediator for dye-sensitized solar cells with conversion efficiency as high as 8.6% [5]. Previously, we observed that the TEMPO radical (1) forms corresponding charge transfer (CT) complexes with appropriate acceptors such as TCNQF4 (3) [6], and even more