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

• grain growth, so the size of the crystalline domain in the film was higher in this case. These larger crystalline domains in films spin-coated from chloroform were beneficial for field effect mobility. None of the OFETs showed any n-type mobility. The extended character of the HOMO residing on the

• dithienyl-thieno-TTF unit and the localised nature of the LUMO led to donor–acceptor interactions in the solid phase, making it impossible for efficient overlap between LUMOs, which would normally be required for an efficient n-type semiconductor. BHJSCs were fabricated from 48 as the electron donor and

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• introduces a high caliber of these molecular complexes. The RCM protocol has been successfully employed to generate a series of dicyanobiphenylcyclophanes 202 which are useful as n-type semiconductors [156]. Winkelmann and co-workers [157] have synthesized chiral concave imidazolinium salts 203 as precursors

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

• suggests that the improvement in OFET performance with the addition of PFBT is due to improved charge injection, rather than an improvement in the morphology of the film. The OFETs were tested for n-type mobility but there was no field-effect observed. Interestingly, despite OFETs fabricated from compound

An integrated photocatalytic/enzymatic system for the reduction of CO₂ to methanol in bioglycerol–water

• Michele Aresta,
• Angela Dibenedetto,
• Tomasz Baran,
• Antonella Angelini,
• Przemysław Łabuz and
• Wojciech Macyk

Beilstein J. Org. Chem. 2014, 10, 2556–2565, doi:10.3762/bjoc.10.267

• by the Kubelka–Munk function. The properties of the photocatalysts used can be summarized as follows. Cu2O is a visible-light-absorbing, red-colored, p-type semiconductor with the band gap energy equal of 2.1 eV. InVO4 is an n-type semiconductor (Ebg = 2.8 eV). TiO2 modified with the organic compound

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

• utilized 3 – while the solid-state structure of 3 showed several sub-van der Waals contact distances, the n-type mobility of the OFET was very low (2 × 10−5 cm2 V−1 s−1) [14]. On the other hand, an OFET utilizing 4 (X = F) had measured electron mobilities of 0.17 cm2 V−1 s−1, and its X-ray crystal

Structure/affinity studies in the bicyclo-DNA series: Synthesis and properties of oligonucleotides containing bc^en-T and iso-tricyclo-T nucleosides

• Branislav Dugovic,
• Michael Wagner and
• Christian J. Leumann

Beilstein J. Org. Chem. 2014, 10, 1840–1847, doi:10.3762/bjoc.10.194

• molecules (Mol A and Mol B) of which the furanose part in Mol A adopts a 2’-endo (S-type) conformation, while in Mol B a 4’-endo (N-type) conformation is observed. In summary it appears that rigidifying and planarizing the C5’–C6’-bond as in tc-nucleosides leads to an anticlinal orientation of torsion angle

• γ and variability between S- and N-type in the furanose conformation, whereas rigidifying and planarizing the C6’–C7’-bond, as in 8β and 11β, leads to a synclinal torsion angle γ and a consistent 2’-endo furanose conformation. Saturation of the carbocyclic ring, as in bc-T, leads to an anticlinal

• prefers RNA over DNA as a complement which is remarkable given that the parent nucleoside adopts a 2’-endo (S-type) sugar conformation and not a 3’endo (N-type) as do modifications that typically prefer RNA as complement (e.g., LNA). This is somewhat similar to observations with the α-L-LNA analogue which

Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction

• Marina Rubina,
• William M. Sherrill,
• Alexey Yu. Barkov and
• Michael Rubin

Beilstein J. Org. Chem. 2014, 10, 1536–1548, doi:10.3762/bjoc.10.158

• regio- and enantioselectivities. On the other hand, superior results were obtained using chiral ligands of the P,N-type [15][41][42][43][44]. Particularly, excellent enantioselectivities were achieved using different variations of phosphanyl-oxazoline (PHOX) ligands [45][46][47][48][49][50][51][52

Stereoselective synthesis of the C79–C97 fragment of symbiodinolide

• Hiroyoshi Takamura,
• Takayuki Fujiwara,
• Isao Kadota and
• Daisuke Uemura

Beilstein J. Org. Chem. 2013, 9, 1931–1935, doi:10.3762/bjoc.9.228

• ), was isolated from the 80% aqueous ethanol extract of the cultured symbiotic dinoflagellate Symbiodinium sp. in 2007 [1]. Symbiodinolide shows voltage-dependent N-type Ca2+ channel-opening activity at 7 nmol/L and COX-1 inhibitory effect at 2 μmol/L (65% inhibition). Furthermore, 1 ruptures the tissue

Molecular assembly of amino acid interlinked, topologically symmetric, π-complementary donor–acceptor–donor triads

• M. B. Avinash,
• K. V. Sandeepa and
• T. Govindaraju

Beilstein J. Org. Chem. 2013, 9, 1565–1571, doi:10.3762/bjoc.9.178

• system due to topological symmetry in their molecular structure and complementary π-character. Since NDI is one of the most promising organic n-type semiconductors, we anticipated that alternative stacking with a special donor such as pyrene would lead to facile charge-transfer interactions. Moreover, 1D

Interplay of ortho- with spiro-cyclisation during iminyl radical closures onto arenes and heteroarenes

• Roy T. McBurney and
• John C. Walton

Beilstein J. Org. Chem. 2013, 9, 1083–1092, doi:10.3762/bjoc.9.120

• literature data for ArCMe=N• type radicals [36][37]. Simulation of the second species indicated one large and four smaller doublet hyperfine splittings (hfs) characteristic of a cyclohexadienyl type radical (Table 1). This spectrum was evidently due to the intermediate from addition of some radical meta to

• the tert-butyl substituent of the solvent. It is known that ArCMe=N• type radicals do not add to t-BuPh under EPR conditions [19][37] neither do EtO• radicals (from dissociation of 6), and hence, we assign this spectrum to the ethoxycarbonyloxyl adduct 9a. This identification was supported by a DFT

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

• Jiří Kulhánek and
• Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

• ]. As a materials researcher, Sellinger applied these n-type conjugated materials as small-molecule electron acceptors. The combination of V-BT (114) with polyhexylthiophene donor (P3HT) in an initial organic solar cell showed high external quantum efficiencies exceeding 14%. Sellinger’s further efforts

Sexithiophenes as efficient luminescence quenchers of quantum dots

• Christopher R. Mason,
• Yang Li,
• Paul O’Brien,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202

• perfluoroalkyl groups for n-type semiconductors [12][13]. Previously, we reported the synthesis and properties of alkyl end-capped oligothiophenes 2 (Figure 1), which incorporate the ethylene dithiothiophene (EDTT) unit, including their performance as the electron donor material in a bilayer photovoltaic device

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• examples of sp3 C–H bond insertion via a cationic gold(I)–carbenoid intermediate. 4.3 Cycloadditions Intramolecular [M + N]-type cycloaddition reactions are powerful tools for accessing complex molecular frameworks [98]. Several gold-catalyzed [3 + 2] [99], [4 + 2] [100][101][102][103][104][105], and [4

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

• studies of trialkoxybenzamide-functionalized quaterthiophene derivative T1 (Scheme 1). We also present our initial results on the morphology of blends of this electron-rich p-type semiconducting T1 with the well-known n-type semiconductor [6,6]-phenyl-C61-butyric acid methyl ester (PCBM). Results and

• concentration of 5 x 10−5 M. Studies on blends of T1 with PCBM The fullerene derivative [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) is a well-known n-type semiconductor and its blends with various electron-donor materials have been extensively used in solar cell devices [24]. The morphology of the blend

• of donor and acceptor materials plays a prominent role in device performance [25]. Recently, we reported that a n-type perylene bisimide organogelator exhibits photovoltaic activity with a p-type semiconducting polymer [26]. In this work, as an initial study we characterized the morphology of a