Effects of solvent additive on “s-shaped” curves in solution-processed small molecule solar cells

• John A. Love,
• Shu-Hua Chou,
• Ye Huang,
• Guilllermo C. Bazan and
• Thuc-Quyen Nguyen

Beilstein J. Org. Chem. 2016, 12, 2543–2555, doi:10.3762/bjoc.12.249

• successfully used cyanoacetate [15] and other electron-withdrawing end groups to create A–D–A type oligothiophene derivatives with tunable electronics, which are among the highest performing materials to date [16][17][18][19]. Starting with the previously reported molecule benzo[1,2-b:4,5-b]bis(4,4′-dihexyl-4H

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

• ), quinquethiophene) were synthesised to examine the influence of chromophore extension on the device performance and stability for OPV applications. The BTxR (x = 4, butyl, and x = 8, octyl) series of materials were synthesised by varying the oligothiophene π-bridge alkyl substituent to examine structure–property

• translated to a second series of products where the oligothiophene sidechain length for the parent (BTR) was systematically varied, i.e. BTxR, where x = 4 (butyl), or 8 (octyl). Incorporation of the BXR series in devices with PC71BM has demonstrated that with increasing chromophore length, the thermal

• in formation of the key intermediates 3a–c, after distillation, in high yield of 60–70% (see refs [16][17][18] for recent similar chemistry). Intermediate 3b has been scaled to the mole scale with no issues noted. With 3a–c in hand, synthesis of the required series of alkyl substituted oligothiophene

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

• 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

• minimize the synthesis efforts, structurally symmetric oligothiophene units are mostly used for constructing A–π–D–π–A-type molecules with a BDT core. Interestingly, although various terthiophene-based derivatives with a BDT core have been reported, there is only one paper that reported the synthesis and

• characterization of BDT derivatives based on oligothiophene π-bridges with more than three thiophene units [27], where symmetric quater- and quinquethiophenes were used as the π-conjugation bridge. Surprisingly, the quaterthiophene-bridged compound showed the worst photovoltaic performance when blending with a

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

• . In some cases poly(ethynylene/vinylene) homologues will be considered for comparison. Additionally, monodispersed tetrathiafulvalene-oligothiophene (TTF-OT) conjugated systems will be discussed as their well-defined structures provide a stronger insight into structure–property relationships. Review

• separation and is lacking efficient electron mobility. TTF-oligothiophene systems with well-defined structures The monodisperse analogue of polymer 34, bearing two TTF units and capped with dodecyl chains at the terminal positions, was synthesised using chemical coupling protocols, or alternatively via

Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin

• Jun Terao,
• Yohei Konoshima,
• Akitoshi Matono,
• Hiroshi Masai,
• Tetsuaki Fujihara and
• Yasushi Tsuji

Beilstein J. Org. Chem. 2014, 10, 2800–2808, doi:10.3762/bjoc.10.297

• -phenylene) and oligothiophene with a pseudo-linked [3]rotaxane structure by full rotation of glucopyranose units via a flipping (tumbling) mechanism in the π-conjugated guest having two permethylated β-cyclodextrin units at both ends. We also succeeded in the synthesis of an organic-soluble fixed [3

• ]rotaxane by a cross-coupling or complexation reaction of thus formed pseudo linked [3]rotaxane. Oligo(para-phenylene), oligothiophene, and porphyrin derivatives were used as π-conjugated guests with stopper groups. Keywords: cross-coupling reaction; insulated π-conjugated molecule; oligothiophene

• -phenylene) [23] and oligothiophene [24] with linked [3]rotaxane structures via the flipping phenomenon [25]. Results and Discussion Kano and co-workers reported the synthesis of a linked pseudo [3]rotaxane involving a water-soluble porphyrin unit with carboxylate groups as the guest unit by double self

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

• +0.73 V. In both cases, the first oxidation wave is assigned to the formation of the radical cation on one of the bi/terthiophene segments of the molecule. The lower oxidation potential for 10 compared to 9 is consistent with the tendency to decrease the oxidation potential when the oligothiophene chain

• are due to the reduction of the DPP and BODIPY moieties. By analogy, the reduction waves at higher negative potentials can be due to the reduction of the oligothiophene units, with 10 having a lower reduction potential for the reduction of the thiophenes because of the extended conjugated chain. The

• more complex picture. The BODIPY units act as a stronger acceptor than the DPP core, causing the overall electrostatic potential charge of the DPP-oligothiophene unit to be positive. This is observed in all three redox states, with the more conjugated compound 10 more positive in each case. Thus, the

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

• 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

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

• their photophysical properties is of great relevance, given the importance of oligothiophene and tpy-units as electro- and photoactive conjugated materials [21][28][29][30][31][32]. Besides these linear counterparts, various tpy-containing polymeric and dendritic structures have been developed and their

• -functionalization of oligothiophene dendrons with optically and/or redox active perylenebisimide, phthalocyanine and quinoxaline units have been developed as possible light-harvesting molecules [43][44][45]. We report herein the synthesis of oligothienylene-ethynylene based 3-dimensional molecular materials, namely

Ring-opening reaction of 2,5-dioctyldithieno[2,3-b:3',2'-d]thiophene in the presence of aryllithium reagents

• Hao Zhong,
• Jianwu Shi,
• Jianxun Kang,
• Shaomin Wang,
• Xinming Liu and
• Hua Wang

Beilstein J. Org. Chem. 2013, 9, 767–774, doi:10.3762/bjoc.9.87

• electrical properties, the derivatives of dithieno[2,3-b:3',2'-d]thiophene (DTT), as one type of fused oligothiophene, have shown their potential applications in organic electronics [1][2][3][4]. The work on the synthesis of DTT derivatives and the chemical stability of the DTT core is of particular interest

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

• study the role of the dimethylaminophenyl group on the oligothiophene properties. The synthesis of 2a and 2b was completed by following our published procedure [14], with oxidative coupling of 3a or 3b with the aid of FeCl3 affording sexithiophenes 2a and 2b in moderate yields (40% and 50%, respectively

• , while the high-energy absorption edge for the nanocrystals is 657 nm. Comparison with the absorption profiles for 1b and 2b confirms that no overlap occurs between the emission from the quantum dot and the absorption by the oligothiophene (Figure 5). As such, any luminescence quenching observed would

• concentrations of ca. 10−3 M, together with n-Bu4NPF6 (0.1 M) as the supporting electrolyte. Under these conditions, the redox potential for the FcH/FcH+ couple was +0.48 V (CH2Cl2, versus Ag/AgCl). The photoluminescence properties of the oligothiophene and CdSe(ZnS) quantum dot blends were measured on a Spex

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

• electron-rich quaterthiophene derivative with the electron acceptor [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) revealed a nanoscale segregated assembly of the individual building blocks in the blend. Keywords: charge transport; hydrogen bonding; oligothiophene; organogel; self-assembly

• bisimides [10][11][12], acenes [13][14] and merocyanines [15][16] have been studied in recent years. Self-assembly of various oligothiophene derivatives have been extensively investigated on account of their semiconducting and optoelectronic properties [17]. Feringa and co-workers reported organogels based

• -containing building block 6 in 78% yield. 2, 2´-Bithiophene was converted to the corresponding tributyltin derivative 8 by the reported procedure [19] and then coupled with compound 6 in the presence of a Pd-catalyst to give the desired oligothiophene derivative T1 in 82% yield. The new compounds 6 and T1