Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

• Desta Gedefaw,
• Marta Tessarolo,
• Margherita Bolognesi,
• Mario Prosa,
• Renee Kroon,
• Wenliu Zhuang,
• Patrik Henriksson,
• Kim Bini,
• Ergang Wang,
• Michele Muccini,
• Mirko Seri and
• Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

• was calibrated by measuring the ferrocene/ferrocenium (Fc/Fc+) redox peak. The HOMO and LUMO energy levels of the polymers and electron acceptors were calculated from the peak values of the third scans by setting the oxidative peak potential of Fc/Fc+ vs the normal-hydrogen electrode (NHE) to 0.630 V

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• the fields of supramolecular and materials chemistry due to their great potential application in molecular electronics, for example, as switches and conductors [10][11][12][13][14]. As we all know, TTF derivatives can form charge transfer (CT) complexes with electron acceptors such as

Photoinduced 1,2,3,4-tetrahydropyridine ring conversions

• Baiba Turovska,
• Henning Lund,
• Viesturs Lūsis,
• Anna Lielpētere,
• Edvards Liepiņš,
• Sergejs Beljakovs,
• Inguna Goba and
• Jānis Stradiņš

Beilstein J. Org. Chem. 2015, 11, 2166–2170, doi:10.3762/bjoc.11.234

• corresponding ground state species. The reaction between photochemically generated radical cations and radical anions by electron transfer from photoexcited electron donor to electron acceptors is often reversible [37] thus reproducing the reactant pair without the formation of a chemical bond. As the dioxygen

Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis

• David W. Manley and
• John C. Walton

Beilstein J. Org. Chem. 2015, 11, 1570–1582, doi:10.3762/bjoc.11.173

• 64 but a significant quantity of ring opened byproduct was also formed. Carbonyl compounds are also good electron acceptors and so SCPC hydrogenations seemed likely. Actually there is a literature precedent for photocatalytic hydrogenation of acetophenone derivatives with TiO2 [80][81]. We studied a

Carboxylated dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, electronic properties, and complexation with zinc ions

• Yunfei Wang and
• Yuming Zhao

Beilstein J. Org. Chem. 2015, 11, 957–965, doi:10.3762/bjoc.11.107

• materials and supramolecular assemblies [1][2][3][4][5], since the first discovery by Wudl and others in the early 1970s that TTF upon interactions with suitable electron acceptors could give rise to charge-transfer complexes exhibiting excellent metallic conductivity [6][7]. The remarkable electron

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

• Huixin Jiang,
• Virginia Mazzanti,
• Christian R. Parker,
• Søren Lindbæk Broman,
• Jens Heide Wallberg,
• Karol Lušpai,
• Adam Brincko,
• Henrik G. Kjaergaard,
• Anders Kadziola,
• Peter Rapta,
• Ole Hammerich and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104

• -energy bands to charge-transfer absorptions, which are usually observed in π-conjugated systems containing TTF donors and large acetylenic scaffolds that behave as electron acceptors [8][9][10]. The significant redshifts of the charge-transfer absorptions experienced for 8 and 2a relative to the

Copper ion salts of arylthiotetrathiafulvalenes: synthesis, structure diversity and magnetic properties

• Longfei Ma,
• Jibin Sun,
• Xiaofeng Lu,
• Shangxi Zhang,
• Hui Qi,
• Lei Liu,
• Yongliang Shao and
• Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 850–859, doi:10.3762/bjoc.11.95

• -based conducting materials are mainly produced as radical cation salts by electrochemical oxidation and CT complexes by chemical oxidation with electron acceptors [5][6]. Most Ar-S-TTFs possess redox potentials higher than that of bis(ethylenedithio)-TTF (BEDT-TTF) [33][34][35][36][37][38][39

• ]. Consequently, the complexes of Ar-S-TTFs with electron acceptors such as fullerenes [40][41] and TCNQ [42] show a neutral ground state. However, Ar-S-TTFs can be chemically oxidized by strong electron acceptors such as F4TCNQ [42] and Keggin-type phosphomolybdic acid [43] to form CT complexes. In comparison

Palladium-catalysed cross-coupling reaction of ultra-stabilised 2-aryl-1,3-dihydro-1H-benzo[d]1,3,2-diazaborole compounds with aryl bromides: A direct protocol for the preparation of unsymmetrical biaryls

• Siphamandla Sithebe and
• Ross S. Robinson

Beilstein J. Org. Chem. 2014, 10, 1107–1113, doi:10.3762/bjoc.10.109

• characteristics, fluoride ion sensing abilities, emissive as well as electron-transporting properties [8][9][10][11]. Three-coordinate boron compounds are electron-poor and strong π-electron acceptors owing to the empty boron pz-orbital, which is capable of significant delocalisation when attached to an organic π

Tuning the interactions between electron spins in fullerene-based triad systems

• Maria A. Lebedeva,
• Thomas W. Chamberlain,
• E. Stephen Davies,
• Bradley E. Thomas,
• Martin Schröder and
• Andrei N. Khlobystov

Beilstein J. Org. Chem. 2014, 10, 332–343, doi:10.3762/bjoc.10.31

• of N@C60–N@C60 molecules [5][6][7]. However the application of these systems is limited due to a number of synthetic challenges associated with the preparation and purification of endohedral fullerenes [8]. This notwithstanding, fullerene cages are excellent electron acceptors and can support up to

Enhancement of efficiency in organic photovoltaic devices containing self-complementary hydrogen-bonding domains

• Rohan J. Kumar,
• Jegadesan Subbiah and
• Andrew B. Holmes

Beilstein J. Org. Chem. 2013, 9, 1102–1110, doi:10.3762/bjoc.9.122

• reported for compound 1 [20] and are suitable for charge transfer to take place to fullerene-based electron acceptors, such as PC61BM. The NH cyanopyridone unit can presumably exist as a number of tautomers; however, if present, these do not appear to affect the electronic properties in solution

Control over molecular motion using the cis–trans photoisomerization of the azo group

• Estíbaliz Merino and
• María Ribagorda

Beilstein J. Org. Chem. 2012, 8, 1071–1090, doi:10.3762/bjoc.8.119

• with π→π* transition is shifted to red, changing the appearance order with respect to the band n→π*. The azocompounds of this type present donor substituents (X) and electron acceptors (Y) at the 4 and 4' positions, respectively (push/pull system) (red colour). The isomerization process normally

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

• devices, etc [1][2][3]. A typical one-component organic D-π-A chromophore consists of a π-conjugated system end-capped with strong electron donors D (e.g. NR2 or OR groups) and strong electron acceptors A (e.g. NO2 or CN groups). This D-π-A arrangement assures efficient intramolecular charge transfer (ICT

• ]. 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

• interest for materials chemists due to their unique and tunable properties. In general, the imidazole-derived chromophores may possess two Y-shaped arrangements: One electron donor at C2 and two electron acceptors at C4/C5 or vice versa. Hence, according to the C4/C5 substitution, the entire imidazole

Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan

• Axel G. Griesbeck,
• Jörg Neudörfl and
• Alan de Kiff

Beilstein J. Org. Chem. 2011, 7, 518–524, doi:10.3762/bjoc.7.60

• Norrish cleavage. The tryptophan derivative 10 is photochemically inert and shows preferential decarboxylation only when induced by intermolecular PET. Keywords: amino acids; decarboxylation; electron transfer; photochemistry; phthalimides; Introduction Phthalimides are versatile electron acceptors in

• +, electronically excited phthalimides are potent electron acceptors [2]. The rich photochemistry of this chromophore has recently been reviewed [3][4]. Intramolecular hydrogen abstraction is an archetype process for electronically excited carbonyl groups (Norrish type II reaction). The 1,4-biradicals formed by γ

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

• visible exhibiting blue or dark green colours, small band gaps and high charge carrier mobilities. They are suitable as electron donor in bulk heterojunction solar cells with PC60BM or PC70BM as electron acceptors to give maximum power conversion efficiencies of about 5%. In field-effect transistors they

Photosonochemical catalytic ring opening of α-epoxyketones

• Hamid R. Memarian and
• Ali Saffar-Teluri

Beilstein J. Org. Chem. 2007, 3, No. 2, doi:10.1186/1860-5397-3-2

• . [7][8][9][10][11][12][13][14][15][16][17] It is well known that the substituted pyridinium cations are good electron acceptors. [18] Garcia and coworkers have used N-alkyl-2,4,6-triphenylpyridinium tetrafluoroborate as photosensitizer in the photochemical cyclization of 5-methyl-4-hexenoic acid to

• and α-epoxyketones have also occurred thermally or photochemically by the presence of various electron acceptors. These reactions have been observed thermally by ceric ammonium nitrate (CAN), [28][29] 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) [30] and iron(III) chloride [31] or photo-induced