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

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

• -accepting diketopyrrolopyrrole (DPP) arms, and its linear analogue, TTA-DPP4 and TTA-DPP2 (Figure 1). TTA can be regarded as a promising central core unit for star-shaped π-conjugated oligomers, and has previously been utilized as a building block of semiconducting polymers for OSCs [24] and organic field

• -effect transistors [25][26][27]. To the best of our knowledge, however, there has been no precedent on TTA-based star-shaped and linear π-conjugated oligomers that can be applied to OSCs. Results and Discussion Molecular design and synthesis To develop star-shaped and linear π-conjugated oligomers with

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

• -based copolymers were synthesized, and most of them showed better semiconducting properties in organic field effect transistors (OFETs), bulk-heterojunction (BHJ) solar cells, thermoelectric and electrical memory devices as compared to the counter 3,6-carbazole-based polymers [28][29][30][31][32][33][34

Syntheses of dibenzo[d,d']benzo[2,1-b:3,4-b']difuran derivatives and their application to organic field-effect transistors

• Minh Anh Truong and
• Koji Nakano

Beilstein J. Org. Chem. 2016, 12, 805–812, doi:10.3762/bjoc.12.79

• . Keywords: furan; heteroacenes; organic field-effect transistors; organic semiconductor; Introduction Organic semiconductors have significantly been developed in the past two decades by virtue of their advantages, such as low weight, flexibility, large-area processability, which are different features from

• conventional silicon-based semiconductors. Organic semiconducting materials can be used as active layers in organic field-effect transistors (OFETs) [1][2][3][4][5][6][7], organic light-emitting diodes (OLEDs) [8][9][10], and organic photovoltaics (OPVs) [11][12]. Among many organic semiconducting materials so

• as dibenzo[d,d']benzo[2,1-b:3,4-b']difuran (syn-DBBDF) and dinaphtho[2,3-d:2',3'-d']benzo[2,1-b:3,4-b']difuran (syn-DNBDF) were synthesized. Their photophysical and electrochemical properties were revealed by UV–vis absorption and photoluminescence spectroscopy and cyclic voltammetry. Organic field

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

• ) [5] and organic field effect transistors (OFETs) [6][7], whereas the PEDOT:poly(styrene sulfonate) salt (PEDOT:PSS) was originally investigated for antistatic applications but is now commercially available for its use as a hole-injecting/collecting material for organic light emitting diodes (OLEDs

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

• Rupert G. D. Taylor,
• Joseph Cameron,
• Iain A. Wright,
• Neil Thomson,
• Olena Avramchenko,
• Alexander L. Kanibolotsky,
• Anto R. Inigo,
• Tell Tuttle and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

• functionalisation [3]. This has led to widespread use of TTF-containing compounds in organic photovoltaic (OPV) devices [4][5][6][7] and in organic field effect transistors (OFETs), as both single crystals [8][9] and thin films [10][11] demonstrating charge carrier mobilities of up to 1.2 cm2 V−1 s−1 [2] for single

• interactions cause destabilisation of the HOMO of 2. The HOMO energies determined from the DFT calculations (Supporting Information File 1, Figure SI1) show that the HOMO of 1 (−6.61 eV) is lower in energy that that of 2 (−6.50 eV), which is consistent with the observed experimental trend. Organic field-effect

• transistors (OFETs) Compounds 1 and 2 were used in the fabrication of bottom-gate bottom-contact OFETs to give an indication on the applicability of these small molecules to organic semiconductor devices. The use of self-assembled monolayers (SAMs) was investigated with pentafluorobenzenethiol (PFBT) and

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

• Miriam Goll,
• Adrian Ruff,
• Erna Muks,
• Felix Goerigk,
• Beatrice Omiecienski,
• Ines Ruff,
• Rafael C. González-Cano,
• Juan T. Lopez Navarrete,
• M. Carmen Ruiz Delgado and
• Sabine Ludwigs

Beilstein J. Org. Chem. 2015, 11, 335–347, doi:10.3762/bjoc.11.39

• , especially the position of the HOMO level and the HOMO–LUMO band gap value are crucial for the applicability in different devices such as organic photovoltaics, organic field effect transistors, organic light emitting diodes or organic electrochromic windows [1][2][3][4][5][6]. There are different ways to

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

• organic field-effect transistors [24][25]. The DPP-based conjugated polymers usually show good electron and hole mobility and promising PCE values in OPVs due to large intermolecular interactions through π–π stacking. Nguyen et al. have investigated the DPP core in small molecules for OPVs with excellent

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

• Bradley D. Rose,
• Peter J. Santa Maria,
• Aaron G. Fix,
• Chris L. Vonnegut,
• Lev N. Zakharov,
• Sean R. Parkin and
• Michael M. Haley

Beilstein J. Org. Chem. 2014, 10, 2122–2130, doi:10.3762/bjoc.10.219

• heteroatoms, etc.) [1][2][3]. Recently there has been resurging interest in PCHs for use as active materials in organic electronic devices. Some popular examples of devices undergoing extensive exploration are organic field effect transistors (OFET) [4][5], organic photovoltaics (OPV) [6], and organic light

Lateral ordering of PTCDA on the clean and the oxygen pre-covered Cu(100) surface investigated by scanning tunneling microscopy and low energy electron diffraction

• Stefan Gärtner,
• Benjamin Fiedler,
• Oliver Bauer,
• Antonela Marele and
• Moritz M. Sokolowski

Beilstein J. Org. Chem. 2014, 10, 2055–2064, doi:10.3762/bjoc.10.213

• to that of PTCDA bulk lattice planes. Keywords: Cu(100); LEED; PTCDA; STM; template; thin organic films; Introduction Interfaces between organic semiconductors and metals have gained large interest because they are present in many applications, e.g., organic field-effect transistors [1] or organic

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

• organic electronic devices based on liquid crystalline semiconductors are low-cost and thus are especially attractive to industry. Until now, DLCs have been explored as active materials applied in organic light-emitting diodes (OLEDs) [13][14][15], organic field-effect transistors (OFETs) [5][6][7][8][16

Crystal design using multipolar electrostatic interactions: A concept study for organic electronics

• Peer Kirsch,
• Qiong Tong and
• Harald Untenecker

Beilstein J. Org. Chem. 2013, 9, 2367–2373, doi:10.3762/bjoc.9.272

• found practical application in printed circuits for driving e-paper displays [1][2]. Among the most critical parameters for their application in organic field effect transistors (OFET) are their charge carrier mobility and their solubility in non-toxic organic solvents for processing by printing

Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles

• Daniel J. Tate,
• Rémi Anémian,
• Richard J. Bushby,
• Suwat Nanan,
• Stuart L. Warriner and
• and Benjamin J. Whitaker

Beilstein J. Org. Chem. 2012, 8, 120–128, doi:10.3762/bjoc.8.14

• -flight; Introduction Liquid crystalline semiconductors [1][2] are potentially useful in the fabrication of organic field-effect transistors [3][4], light-emitting devices [5][6][7] and photovoltaic devices [8][9][10][11]. Most of the interest has centred on using them as hole conductors and a lot of

Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

• Filipe Vilela,
• Peter J. Skabara,
• Christopher R. Mason,
• Thomas D. J. Westgate,
• Asun Luquin,
• Simon J. Coles and
• Michael B. Hursthouse

Beilstein J. Org. Chem. 2010, 6, 1002–1014, doi:10.3762/bjoc.6.113

• motif for materials applications. For example, benzyl and thienyl annelated TTF derivatives and analogues have been shown to perform well as semiconductor materials in organic field effect transistors (OFETs) [21][22]. This has been attributed to the enhanced π–π stacking of the extended aromatic groups

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• characteristic properties of the polymers are described. Potential applications in the field of organic electronic materials such as light emitting diodes, organic solar cells and organic field effect transistors are discussed. Keywords: conjugated polymer; diketopyrrolopyrrole; electroluminescence

Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases

• Eugen Wuckert,
• Constanze Hägele,
• Frank Giesselmann,
• Angelika Baro and
• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 57, doi:10.3762/bjoc.5.57

• organic field effect transistors, organic photovoltaic devices and light emitting diodes [1][2][3]. Tetraphenylenes, whose saddle-shaped conformation is caused by the anti-aromatic character of the corresponding central flat 8-membered ring [4][5][6], are suitable building blocks for supramolecular

The efficient synthesis of dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene and cyclopenta[1,2-b:4,3-b′]bis(benzo[d]thiophen)-6-one

• Zhihua Wang,
• Sheng Zhu,
• Jianwu Shi and
• Hua Wang

Beilstein J. Org. Chem. 2009, 5, No. 55, doi:10.3762/bjoc.5.55

• fabricate organic field-effect transistors (OFETs) [1][2][3][4][5][6][7], light emitting diodes (LEDs) [8][9], and photovoltaic cells [10]. Various novel π-extended heteroarenes, e.g. dibenzo[d,d′]thieno[3,2-b:4,5-b′]dithiophene [11], pentathienoacene [12], and benzo[1,2-b:4,5-b′]bis[b]benzothiophene [13

Progress in liquid crystal chemistry

• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 48, doi:10.3762/bjoc.5.48

• organic light emitting diodes, photovoltaic devices, organic field effect transistors, gas sensors etc. [3][4][5][6][7][8]. One of the major issues in liquid crystal research today is still the poor knowledge of structure-property relationships and thus the synthesis of whole series of structurally