Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• (Voc), underscored the influence of the molecular structure [23]. A recent development by Liang et al. introduced Qx-derived double-cable conjugated polymers as a promising approach for improving the performance of single-component-OSCs (SCOSCs). They replaced the traditional benzothiadiazole core of Y

• , resulting in an efficiency of 18% and marking a significant advancement in OSC research [27]. Zhou and co-workers synthesized Y6-type NFA acceptors, Qx12 and Qx13, by substituting Y6’s benzothiadiazole ring with a Qx moiety. Qx13 exhibited a stronger π–π interaction compared to Qx12, which facilitated

• -based dyes, Qx39–Qx42 and the resulting device performance were highlighted by Huang et al. The use of quinoxaline-dithienothiophene and phenazine-dithienothiophene as π-bridges with the benzothiadiazole moiety as an auxiliary group did not yield the expected improvement, potentially due to the non

Chemical syntheses and salient features of azulene-containing homo- and copolymers

• Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

• -dibromo-[2-(3-dodecylthien-2-yl)]azulene (46) by using two successive Suzuki coupling reactions with thiophene boron ester 47 and biphenyl-4,4’-diboronic acid bis(pinacol) ester 49 (Scheme 11), whereas the Suzuki coupling of 46 with 2,1,3-benzothiadiazole-4,7-bis(boronic acid pinacol ester) 51 yielded the

• decomposition temperature, which was over 350 °C. The polymers 50, 54, and 56 exhibited absorption bands in the 400–450 nm range due to π–π* transition. However, polymer 52, which contains a benzothiadiazole ring was an exception, as it showed a highly red-shifted band at 550 nm. The important feature of these

• discouraged the protonation. In 2013, Xu and co-workers [42] reported the synthesis of azulene-fluorene-benzothiadiazole terpolymers 136–138, containing varying degrees of azulene and benzothiadiazole units in good yields by adopting the Suzuki coupling protocol (Scheme 23). The polymers 136–138 were of

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• in the length and structure of the thiophene chain, nor the presence of an embedded benzothiadiazole fragment led to an improvement in the characteristics of transistors based on compounds 39–43 [70][71][72][73]. These derivatives had only hole-type conductivity in the range μh = 1.5⋅10−4–6⋅10−6 cm2

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• synthesized [163]. A synthesis of C60 fullerene conjugate 214 with a benzothiadiazole moiety is shown in Scheme 45, while Scheme 46 presents a synthetic pathway to diketopyrrolopyrrole-modified conjugate 215. Other methanofullerenes without aromatic groups obtained by this method are presented below

• fullerene array 213. The synthetic route to conjugates 214 of fullerene with benzothiadiazole. The synthetic route to conjugates 215 of fullerene with diketopyrrolopyrrole. The synthetic route to fullerene–acetylene hybrids. [60]PCBM derivatives containing various aromatic and alkyl groups bound to the C60

Dawn of a new era in industrial photochemistry: the scale-up of micro- and mesostructured photoreactors

• Emine Kayahan,
• Mathias Jacobs,
• Leen Braeken,
• Leen C.J. Thomassen,
• Simon Kuhn,
• Tom van Gerven and
• M. Enis Leblebici

Beilstein J. Org. Chem. 2020, 16, 2484–2504, doi:10.3762/bjoc.16.202

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• subsequently cross-linked by oxidative homocoupling to form a highly cross-linked polymer [138]. Zhang and co-workers recently demonstrated that the dispersibility of polymer nanoparticle-supported benzothiadiazole photocatalysts could be improved in a range of different solvents by copolymerising classical

Plasma membrane imaging with a fluorescent benzothiadiazole derivative

• Pedro H. P. R. Carvalho,
• Jose R. Correa,
• Karen L. R. Paiva,
• Daniel F. S. Machado,
• Jackson D. Scholten and
• Brenno A. D. Neto

Beilstein J. Org. Chem. 2019, 15, 2644–2654, doi:10.3762/bjoc.15.257

• , Brazil Laboratory of Molecular Catalysis, Institute of Chemistry, Graduate Program (PPGQ), Universidade Federal do Rio Grande do Sul, Porto Alegre, RS, 91501-970, Brazil 10.3762/bjoc.15.257 Abstract This work describes a novel fluorescent 2,1,3-benzothiadiazole derivative designed to act as a water

• for all tested models. Keywords: benzothiadiazole; bioprobe; cell imaging; fluorescence; mitochondria; molecular architecture; plasma membrane; Introduction The selective staining of plasma membranes is of paramount importance to study cellular processes and events associated with this dynamic

• application of water-soluble plasma membrane probes [17][18]. We have been developing a new class of selective bioprobes based on the derivatization of the 2,1,3-benzothiadiazole (BTD) core (Figure 1) [19][20][21][22]. After we disclosed the use of these BTD derivatives as a new class of selective

Synthesis of dipolar molecular rotors as linkers for metal-organic frameworks

• Sebastian Hamer,
• Fynn Röhricht,
• Marius Jakoby,
• Ian A. Howard,
• Xianghui Zhang,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1331–1338, doi:10.3762/bjoc.15.132

• linkers in MOFs with potential applications as ferroelectric materials and for optical signal processing. Keywords: benzothiadiazole; dipolar rotor; fluorescence; large dipole moment; metal organic framework linker; Introduction Rotors are among the fundamental functional units in engineering in our

• acid 1 using cesium fluoride under a carbon dioxide atmosphere. Difluoro- and dicyanobenzothiadiazole compounds 2 and 3 Substituted benzothiadiazole derivatives are well studied in the literature and are of great interest in organic photovoltaics and electronics. As there are no reports of such

• building blocks in MOF systems yet, both derivatives are promising starting materials for the preparation of functional materials based on MOF structures. Annelated benzothiadiazole linkers could also be obtained following the general synthetic approach as shown in Scheme 3. Synthesis of the difluoro

Molecular-level architectural design using benzothiadiazole-based polymers for photovoltaic applications

• Vinila N. Viswanathan,
• Arun D. Rao,
• Upendra K. Pandey,
• Arul Varman Kesavan and
• Praveen C. Ramamurthy

Beilstein J. Org. Chem. 2017, 13, 863–873, doi:10.3762/bjoc.13.87

• 10.3762/bjoc.13.87 Abstract A series of low band gap, planar conjugated polymers, P1 (PFDTBT), P2 (PFDTDFBT) and P3 (PFDTTBT), based on fluorene and benzothiadiazole, was synthesized. The effect of fluorine substitution and fused aromatic spacers on the optoelectronic and photovoltaic performance was

• endeavored to obtain a series of low band gap polymers, P1, P2, and P3, with matching HOMO–LUMO energy levels with the acceptor moiety, without sacrificing the planarity of the molecule. Benzothiadiazole and fluorene, which are commonly used moieties in D–A–D-type polymers, have been chosen as the acceptor

• nitric acid and acetic acid gave dinitro compound 6. The nitro groups in 6 were then reduced by treatment with iron powder and acetic acid. The cyclization of the diamino compound 7 (as described for compound 1) afforded the difluorinated benzothiadiazole 8. The monomer M2 was obtained by coupling 8 with

Benzothiadiazole oligoene fatty acids: fluorescent dyes with large Stokes shifts

• Lukas J. Patalag and
• Daniel B. Werz

Beilstein J. Org. Chem. 2016, 12, 2739–2747, doi:10.3762/bjoc.12.270

• isomerization has to take place. To access the benzothiadiazole (BTD) fatty acid 3 with just one conjugated double bond we made use of the Wittig reaction starting with commercially available aldehyde 1. As expected, the (Z)-isomer was the major product; thus, we performed a subsequent cis–trans isomerization

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

• ], where D1 is an electron-rich unit such as bithiophene, A is a benzothiadiazole derivative and D2 can be different electron-rich planar cores such as dithienosilol or silanindacenodithiophene. Utilizing this push–pull molecular approach, efficiencies up to 9.0% have been achieved [13] due to deep highest

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

• ., who have reported solar cells incorporating a hybrid thiophene–benzothiadiazole–thiophene–BODIPY derivative with power conversion efficiencies of ca. 1.25% [55]. Whilst the open circuit voltage of our best device was higher than theirs (0.62 V), in Ziessel’s work the fill factor (35%) and short

New core-pyrene π structure organophotocatalysts usable as highly efficient photoinitiators

• Sofia Telitel,
• Frédéric Dumur,
• Thomas Faury,
• Bernadette Graff,
• Mohamad-Ali Tehfe,
• Didier Gigmes,
• Jean-Pierre Fouassier and
• Jacques Lalevée

Beilstein J. Org. Chem. 2013, 9, 877–890, doi:10.3762/bjoc.9.101

• , Py_3, Py_4, Py_9, Py_10) two functionalized triazines (Py_7, Py_12), a triphenylamine (Py_6), a carbazole (Py_11) and a benzothiadiazole (Py_8) (Scheme 3). The idea is to get a high absorption around 380–410 nm where Xe–Hg lamps, Xe lamps, LED, laser diodes and even household halogen lamps are usable

Photoreactions of cyclic sulfite esters: Evidence for diradical intermediates

• Rick C. White,
• Benny E. Arney Jr. and
• Heiko Ihmels

Beilstein J. Org. Chem. 2012, 8, 1208–1212, doi:10.3762/bjoc.8.134

• loss of nitrogen from cyclic azo compounds is stepwise or concerted [6]. The photoextrusion of molecular nitrogen was employed also synthetically in the photoreaction of a benzothiadiazole to give an antiaromatic derivative of benzothiirene [7]. In another case, Griffin proposed carbene intermediates

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57