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

• (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

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

• -effect transistors (OFETs) were fabricated with these compounds as organic semiconductors, and their semiconducting properties were evaluated. OFETs with syn-DBBDF and syn-DNBDF showed typical p-type characteristics with hole mobilities of <1.5 × 10−3 cm2·V−1·s−1 and <1.0 × 10−1 cm2·V−1·s−1, respectively

• . 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

• ']difurans and benzo[1,2-b:6,5-b']difurans) and studied their structure–property relationship [33][34]. Furthermore, naphthodifurans with a fused-naphthalene between two furan rings have been developed as organic semiconductors for OFETs [19][20]. In particular, the naphtho[2,1-b:6,5-b']difuran derivative 2

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

• of the conjugated backbone either directly or via a dithiin ring. The electrochemical behaviour of these materials and structure–property relationships are discussed. The study is directed towards the development of a new type of organic semiconductors based on these hybrid materials for application

• basis of the polaron mechanism and the mixed valence state of doped TTF units has developed now into efforts to use the TTF unit as a handle for controlling the morphology of organic semiconductors in the solid state. The great challenge in this field is to design hybrid materials where the position of

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

• interactions; organic field effect transistor (OFET); organic semiconductors; tetrathiafulvalene; thiazole; Introduction The TTF moiety has received much attention in the field of organic electronics owing to its reliable redox behaviour [1], good charge transport properties [2] and scope for

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

• 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

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

Aryl substitution of pentacenes

• Andreas R. Waterloo,
• Anna-Chiara Sale,
• Dan Lehnherr,
• Frank Hampel and
• Rik R. Tykwinski

Beilstein J. Org. Chem. 2014, 10, 1692–1705, doi:10.3762/bjoc.10.178

• to chemically assemble small organic molecules for such applications, clever design and synthesis have rapidly offered new materials for the nascent era of molecular electronic [4][5][6][7][8][9][10][11]. Prominent p-type organic semiconductors include substituted acenes in general [12][13][14][15

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

• Anastasia S. Kostyuchenko,
• Vyacheslav L.Yurpalov,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2014, 10, 1596–1602, doi:10.3762/bjoc.10.165

• as organic semiconductors in light emitting diodes (OLED’s), field effect transistors (FETs), electrochemical and chemical sensors and other organic electronic devices [1][2][3][4][5]. This family of organic semiconductors is especially interesting because they can be rendered solution processable

• by consequence their electron affinity (EA) and ionization potential (IP) are not appropriate [2]. Since these two parameters determine the redox, spectroscopic, electronic and optoelectronic properties of oligothiophenes, their tuning is of crucial importance in any design of new organic

• semiconductors. One of the possible ways of the preparation of low molecular mass semiconductors, showing higher than oligothiophene IP values, is to synthesize molecules in which a central electron accepting group separates two bi-, ter- or quaterthiophene units. Such compounds containing thiadiazole [10][11

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

• view angles [1][2]. More interestingly, DLCs can self-organize into columnar mesophases with a high degree of order, and show fast unidirectional charge migration properties, and have been studied as soft organic semiconductors [3][4][5][6][7][8][9][10][11][12]. Solution-processed and ink-jet printing

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

• distribution of partial charges are readily available. In contrast to most other acenes, these compounds crystallize with a slipped-stack, brickwork-like packing which is mainly controlled by electrostatic interactions. This type of packing offers an advantage for organic semiconductors, because it allows more

• isotropic charge transport compared to the “herring bone” stacking observed for other acenes. Keywords: aromatic stacking; charge carrier transport; crystal design; electrostatic control; organic semiconductor; organo-fluorine; Introduction Within a very few years the first organic semiconductors have

• experimentally observed charge carrier mobilities, e.g., in pentacene based OFETs, remain far below the theoretically predicted limit of several tens of cm2·V−1s−1 [8]. In order to overcome this obstacle, it would be ideal to have acene-like organic semiconductors which pack in the crystal not in one-dimensional

Synthesis, photophysical and electrochemical characterization of terpyridine-functionalized dendritic oligothiophenes and their Ru(II) complexes

• Amaresh Mishra,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2013, 9, 866–876, doi:10.3762/bjoc.9.100

• ; oligothiophene; spectroscopy; terpyridine; Introduction Research concerning the design, characterization and application of organic semiconductors is carried out intensively due to the attractive prospects of their application in organic and molecular electronics [1][2][3][4][5]. In particular, thiophene-based

• -thiophene dendrons. The core functionalization with a redox and optically active ligand and a corresponding metal complex and the extension of the conjugated π-system via stiff triple bonds [42] should lead to complex 3D organic semiconductors with spatially defined functionalities. Results and Discussion

Novel carbazole–pyridine copolymers by an economical method: synthesis, spectroscopic and thermochemical studies

• Aamer Saeed,
• Madiha Irfan and
• Shahid Ameen Samra

Beilstein J. Org. Chem. 2011, 7, 638–647, doi:10.3762/bjoc.7.75

• has been focused on organic semiconductors, including polymers, oligomers, dendrimers, small molecules and heavy-metal complexes, after the discovery by Burroughes et al. in 1990 [1][2][3][4][5][6] that they can be used for fabricating organic light emitting diodes (OLEDs). A number of criteria exist

Self-assembly and semiconductivity of an oligothiophene supergelator

• Pampa Pratihar,
• Suhrit Ghosh,
• Vladimir Stepanenko,
• Sameer Patwardhan,
• Ferdinand C. Grozema,
• Laurens D. A. Siebbeles and
• Frank Würthner

Beilstein J. Org. Chem. 2010, 6, 1070–1078, doi:10.3762/bjoc.6.122

• amorphous or crystalline organic semiconductors it should be taken into account that the oligothiophene moiety, which is responsible for charge transport, is only 19% of the total molecular weight of T1 and the remainder being made up by long alkyl chains that do not contribute to charge carrier mobility

Self-assembled ordered structures in thin films of HAT5 discotic liquid crystal

• Piero Morales,
• Jan Lagerwall,
• Paolo Vacca,
• Sabine Laschat and
• Giusy Scalia

Beilstein J. Org. Chem. 2010, 6, No. 51, doi:10.3762/bjoc.6.51

• compared to the bulk situation, where the same material crystallizes into a polymorphic structure at 68 °C. Keywords: AFM; discotic liquid crystals; hexapentyloxytriphenylene; self-organization; thin films; Introduction Discotic liquid crystals are an interesting type of organic semiconductors that allow

The subtle balance of weak supramolecular interactions: The hierarchy of halogen and hydrogen bonds in haloanilinium and halopyridinium salts

• Kari Raatikainen,
• Massimo Cametti and
• Kari Rissanen

Beilstein J. Org. Chem. 2010, 6, No. 4, doi:10.3762/bjoc.6.4

• in crystal engineering [18][19], and lately it has widely and successfully applied in other fields of material science, such as in supramolecular separations, liquid crystals, organic semiconductors and paramagnetic materials technologies [20][21]. Recently, the important role of XBs in biological