Mono- and bithiophene-substituted diarylethene photoswitches with emissive open or closed forms

• A. Lennart Schleper,
• Mariano L. Bossi,
• Vladimir N. Belov and
• Stefan W. Hell

Beilstein J. Org. Chem. 2019, 15, 2344–2354, doi:10.3762/bjoc.15.227

• . Oligothiophenes are highly fluorescent [6][7], and therefore, we reasoned that their incorporation into DAEs with oxidized 2-alkylbenzo[b]thiophene units might produce fluorescent open forms in addition to the intrinsic fluorescence of the closed forms. In particular, we expected that the prolonged conjugation

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• DTS 2/DSS 4, respectively, which is explained in theoretical studies by a higher quinoidal character of the oligoselenophenes and a higher twisting barrier of the interring C–C bonds compared to oligothiophenes. The optical energy gaps, Eg, are in accordance with the observed trend and decrease from

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

• hexyl-substituted quater- and quinquethiophenes 8b and 10b, Scheme 2. Conversion of the intermediate TMS-protected oligothiophenes to the iodo-oligothiophenes (n =1 and 2) was achieved using iodine monochloride (ICl), however for n = 3 and 4 a number of side reactions leading to unidentified side

• [19]. An initial reaction screening, investigating ligand, base and solvent variation, showed positive results with up to 32% yield of the required bithiophene 4. We are currently examining catalyst optimization to improve the yields of this simplified route to the required oligothiophenes. To avoid

• active layer morphology investigation for enhanced performance of ternary blend OPV devices are being explored currently and the results will be communicated elsewhere. Conclusion We have reported a simplified synthesis of alkylsubstituted oligothiophenes used as π-bridges in A–π-D–π-A molecular electron

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

• ; copper; cyclic voltammetry; DFT; microwave-assisted synthesis; multicomponent reactions; palladium; phenothiazines; thiophenes; Introduction Oligothiophenes [1][2][3][4][5][6][7][8] have adopted a dominating role among functional π-electron systems [9]. In particular, they have received attention as

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

• of the π-bridges. In this respect, oligothiophenes, including monotiophene [16][20], bithiophene [16], terthiophene [8][14][15][17][18][19][21][22][23][26], quaterthiophene and quinquethiophene [27], and cyclopentadithiophene [28] have been utilized as the π-bridge in constructing conjugated

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

• Abstract The aim of this review is to give an update on current progress in the synthesis, properties and applications of thiophene-based conjugated systems bearing tetrathiafulvalene (TTF) units. We focus mostly on the synthesis of poly- and oligothiophenes with TTF moieties fused to the thiophene units

• oxidation peak of the TTF and the oxidation of the sexithiophene backbone. A series of hybrid electroactive compounds 54 (n = 0–2) with two oligothiophenes directly fused to one TTF unit was recently reported [92][93]. Here, triethylphosphite mediated homo-coupling of the corresponding oligothiophenes 55 (n

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

• crystal devices. Similarly, oligothiophenes have demonstrated excellent properties for use in both light-emitting [12] and light-harvesting devices [11][13]. Previously, our group reported a series of molecules containing various oligothiophenes fused to a TTF moiety through the central thiophene [11][14

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

• processing during device fabrication. The difference in power conversion efficiencies (PCEs) between polymer and small-molecule based OPVs is decreasing and PCEs over 7% have been realised in the case of the latter [18][19]. Small molecules used in OPVs are most commonly based on oligothiophenes and their

• unit derivatives substituted with oligothiophenes at the meso-position [47]. Thus, the incorporation of two extra thiophene rings, and connection to the DPP core, does not affect the absorption peak associated with the BODIPY units. On the other hand, the extension of the π-conjugated system

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

• functionalised oligothiophenes, coupled to other heteroaromatic cores. Keywords: bithiophene; donor–acceptor; luminescence; 1,3,4-oxadiazole; 1,3,4-thiadiazole; 4H-1,2,4-triazole; Introduction In the past two decades oligo- and polythiophenes gained a significant research interest due to their wide application

• 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

• ][12][13][14][15], oxadiazole [14][15][16][17] or tetrazine units [13][18][19][20] have been reported. Moreover, luminescence properties of these derivatives are superior to those of the corresponding penta-ring oligothiophenes. For example, the central heterocycle ring replacement in substituted

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

• photophysical properties studied [33][34][35][36][37][38]. However, to our knowledge, tpy-functionalized dendritic oligothiophenes have not been synthesized so far. The complexation of these dendrons could lead to interesting nanosized materials containing different chromophores to study electronic energy

• -transfer processes. A series of shape-persistent all-thiophene dendrons and dendrimers were recently introduced by Advincula et al. [39][40] and us [41][42]. These dendritic oligothiophenes are excellent model compounds for the study of fundamental photophysical and electronic properties. Furthermore, core

• conditions afforded key tpy-functionalized dendritic oligothiophenes 8 and 9 in 85 and 94% yield, respectively (Scheme 2). In a final step, tpy-ligands 8 and 9, which are soluble in common organic solvents, were then reacted with half an equivalent of [RuCl2(DMSO)4] in a mixture of MeOH/THF to afford the

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

• -b]thiophene [13]. More recently, Nenajdenko et al. reported that fused thieno[2,3-b]thiophenes and some [3,2-b]-fused oligothiophenes were attacked by organo-lithium reagents resulting in the cleavage of thiophene rings [14]. They found when competitive deprotonation of the substrate was possible

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

• dot emission was studied by photoluminescence spectroscopy and compared with the performance of alkyl end-capped sexithiophenes 2a and 2b. Keywords: electrochemistry; luminescence quenching; quantum dots; sexithiophenes; synthesis; Introduction Structurally well-defined oligothiophenes as functional

• deposition [1]. This has led to the application of oligothiophenes in numerous organic devices including solar cells [2][3][4], light-emitting diodes (LEDs) [5][6], field-effect transistors [7][8][9] and electrochromics [10]. Furthermore, end-capped oligothiophenes are particularly attractive materials for

• study due to their enhanced stability, and this can lead to improved performance in devices through enhanced intermolecular ordering [11]. Tailoring of the properties of oligothiophenes can be achieved by the appropriate choice of the end-capping functionality, for example, the incorporation of

Syntheses and properties of thienyl-substituted dithienophenazines

• Annemarie Meyer,
• Eva Sigmund,
• Friedhelm Luppertz,
• Gregor Schnakenburg,
• Immanuel Gadaczek,
• Thomas Bredow,
• Stefan-S. Jester and
• Sigurd Höger

Beilstein J. Org. Chem. 2010, 6, 1180–1187, doi:10.3762/bjoc.6.135

• : oligothiophenes; phenazines; scanning tunneling microscopy; self-assembled monolayers; TD-DFT calculations; Introduction Thiophene based oligomers and polymers have drawn considerable interest as active materials in various fields of organic electronics such as organic light-emitting diodes (OLEDs), organic thin

• of the absorption and emission spectra. Spectral data of oligothiophenes in CH2Cl2.. Lowest vertical excitation energies obtained by B3LYP/TZVP TD-DFT calculations of the quaterthiophene 19 and derivatives as well as sexithiophene 20 and derivatives (gas phase and in CH2Cl2) in eV, and oscillator

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

• -heptane, additional shoulders appeared at 420, 461 and 513 nm that were absent in the spectrum recorded in chloroform. These results are in accord with the literature reports for the formation of H-aggregates of oligothiophenes [19] and can be attributed to an excitonic interaction as well as an increase

• mobility value obtained for T1 is very close to that reported for non-regio regular alkyl-substituted polythiophenes (Σμmin = 7 × 10−3 cm2 V−1 s−1) [29], suggesting similar electronic coupling between oligothiophenes in the gelated π-stacks. Conclusion We have demonstrated the self-assembly and charge

Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines

• Adam W. Franz,
• Svetlana Stoycheva,
• Michael Himmelhaus and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2010, 6, No. 72, doi:10.3762/bjoc.6.72

• gold substrates to solutions of sulfur functionalized molecules [7][8][9][10][11][12][13][14]. These “alligator-clips” [15][16][17] are able to bind functional molecules covalently to gold{111}-surfaces. Phenyl derivatives [18][19], conjugated bi- [18][20] and oligophenyls [18][20][21], oligothiophenes

Effect of transannular interaction on the redox- potentials in a series of bicyclic quinones

• Grigoriy Sereda,
• Jesse Van Heukelom,
• Miles Koppang,
• Sudha Ramreddy and
• Nicole Collins

Beilstein J. Org. Chem. 2006, 2, No. 26, doi:10.1186/1860-5397-2-26

• starting compound. Despite the neglected orbital relaxation that immediately follows the reduction, such correlations have proved to be an efficient tool for prediction of redox-potentials of anthracyclines [5], substituted anthracenes [6], and oligothiophenes [7]. For all chemical species, the