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

• and demonstrated n-type properties due to the electronegative Qx unit [53]. Mikie et al. explored ester-functionalized quinoxalines (QEs) as building units for both p-type and n-type polymers. They synthesized two new π-conjugated polymers, Qx51 and Qx-52, with low-lying HOMO (–5.5 eV) and LUMO (–3.4

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• and emission takes place within the intrinsic region [2][3][4][5][6]. Two families of widely investigated emitters for LEECs are ionic transition metal complexes (iTMCs) [7][8][9][10] and conjugated polymers (CPs) [4]. From the early use of ruthenium(II) complexes, a significant amount of research has

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

• Hengjia Liu and
• Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

• emitters can be realized by adding a Lewis acid to a fluorescent conjugated compound [15][16]. Lewis acids are common complexing agents [17] and are frequently used to dope conjugated polymers to enhance their conductivity while the luminescence is completely quenched [18][19]. In contrast, in the presence

• spectral red-shift of protonated conjugated polymers depended greatly on the strength of the Lewis acid (Figure 3a) [26]. Wang et al. modulated the electron-accepting strength of intramolecular charge transfer molecules by using different acids and obtained four distinctly different solid-state emission

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

• -workers [27][28], in 2004, reported the synthesis of conjugated polymers containing azulene and bithiophene units, called poly{1,3-bis[2-(3-alkylthienyl)]azulene} 33–38. The 1,3-bis(3-alkylthienyl)azulene 32, synthesized by the Grignard reaction of 1,3-dibromoazulene (4) with 2-bromo-3-alkylthiophene, was

• reversible acid–base response, which was evident from its absorption and EPR studies. The optical HOMO–LUMO gap for 45 was smaller in the protonated form (1.50 eV) compared to its neutral form (1.62 eV). In 2014, Wang, He, and co-workers [33][34] synthesized the conjugated polymers containing poly(thienyl

• donor for organic PV cells and the blend of thin-film 69 with PC71BM showed a power conversion efficiency (PCE) of 2.04%. In 2018, Gao and co-workers [37] reported the synthesis of conjugated polymers containing 2,6-connected azulene units in the polymer backbone. The key monomer, N,N’-bis(2

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

• . Transistor characteristics of DPP–isoindigo-conjugated polymers 51 and 52. Transistor characteristics of homopolymers 53–55.a

• substituent as side-chain photon trap. Isoindigo derivatives for OFET technology with the best mobility. Monoisoindigos as low-molecular-weight semiconductors. Polymeric bithiopheneisoindigos for OFET creation. Fluorination as a tool to improve isoindigo-based OFET devices. Diversely DPP–isoindigo-conjugated

• polymers for OFETs. Isoindigoid homopolymers with differing rigidity. Isoindigo-based materials with extended π-conjugation. Poly(isoindigothiophene) compounds as sensors for ammonia. Sensor devices based on poly(isoindigoaryl) compounds. Isoindigo polymers for miscellaneous applications. Mono-, rod-like

Selective recognition of ATP by multivalent nano-assemblies of bisimidazolium amphiphiles through “turn-on” fluorescence response

• Rakesh Biswas,
• Surya Ghosh,
• Shubhra Kanti Bhaumik and
• Supratim Banerjee

Beilstein J. Org. Chem. 2020, 16, 2728–2738, doi:10.3762/bjoc.16.223

• the receptor with their complementary binding partners in the target analyte [15]. One of the ways to design multivalent systems is to connect the receptors through covalent linkages. Conjugated polymers and conjugated polymer electrolytes are prominent examples of covalently constructed multivalent

• [36][37][38], conjugated polymers [39][40][41][42], quantum dots [43][44] and sensors based on organic receptors such as imidazolium, ammonium, guanidinium [45][46][47][48][49][50][51][52], etc. have also been developed. Imidazolium based synthetic receptors typically utilize a combination of

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• furnish compound 132 (Scheme 34). Since polyanilines are interesting π-conjugated polymers that contain characteristic conductivity by acid doping, environmental stability, optical and redox properties. Therefore, bridging of oligoaniline as a spacer between the functional units can lead toward the

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

• . Hence, the charge mobility in organic semiconductors is typically much lower than in crystalline inorganic materials [115]. Conjugated polymers that are rigid will generally have faster intrachain charge transport rather than interlayer hopping transport (Figure 8) [107][115]. The process is highly

• temperature to yield alkyl, halo, and trifluoromethyl products, such as the examples 5 and 6 (Scheme 2). Chen, Wang and co-workers recently studied methods to reduce the exciton binding energy in linear conjugated polymers to enhance the charge separation and subsequent photocatalytic hydrogen evolution

• (Figure 11) [129]. Four conjugated polymers containing dibenzothiophene sulfone (FSO) monomers, linked by either biphenyl (FSO-BP), fluorene (FSO-F), 2,8-dibenzothiophene (FSO-FSz), or 3,7-dibenzothiophene (FSO-FS) monomers were synthesised and applied in the photocatalytic hydrogen evolution reaction

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

• Bernd Strehmel,
• Christian Schmitz,
• Ceren Kütahya,
• Yulian Pang,
• Anke Drewitz and
• Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

• alternatives such as rylenes [56] or conjugated polymers [57] with the focus to receive materials covering a broad absorption range up to the near infrared (NIR) part. Nevertheless, they have not reached the necessary practical use as cyanines explainable by the modest solubility in many industrial matrix

Room-temperature Pd/Ag direct arylation enabled by a radical pathway

• Amy L. Mayhugh and
• Christine K. Luscombe

Beilstein J. Org. Chem. 2020, 16, 384–390, doi:10.3762/bjoc.16.36

• radical; visible light; Introduction π-Conjugated polymers are of significant interest as they have the potential to combine the mechanical flexibility and affordability of synthetic polymers with the optical and electronic properties of semiconductors. One of the limitations to this field’s continued

Synthesis of a [6]rotaxane with singly threaded γ-cyclodextrins as a single stereoisomer

• Jason Yin Hei Man and
• Ho Yu Au-Yeung

Beilstein J. Org. Chem. 2019, 15, 1829–1837, doi:10.3762/bjoc.15.177

• -conjugated polymers [29][30][31]. On the other hand, γ-CD is relatively less employed in the synthesis of mechanically interlocked molecules despite of its ability to form interesting 1:2 inclusion complexes, and there are only few examples of rotaxane and catenane featuring γ-CD as an interlocked macrocycle

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

• oxidatively polymerized to polythiophenes [48][49][50] or polyselenophenes [51], respectively, we were interested in the electropolymerization of heterotriacenes 1–4 to the corresponding conjugated polymers P1–P4. Hence, monomers 1–4 were subjected to potentiodynamic polymerization in dichloromethane/TBAPF6

• conjugated polymers. The related poly(dithienopyrrole) P(DTP) in contrast is more electron-rich and much easier to oxidize (Eonset = −0.54 V vs Fc/Fc+) [47]. Additionally, we evaluated the electrochemical stability of polymers P1–P4. After performing 30 sweeps, about 18–19% of the electroactivity was

• different scan rates (right). Synthesis of heterotriacenes DTT 1 and DTS 2 via copper-catalyzed cross-coupling reactions. Synthesis of selenolotriacenes DST 3 and DSS 4. Oxidative polymerization of heterotriacenes 1–4 to corresponding conjugated polymers P1–P4. Bond distances, bond angles, and distances D

Fluorogenic PNA probes

• Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

• probes with nanomaterials as an external quencher. In addition, the uncharged backbone of PNA offers other unique designs, including the combination of PNA probes with cationic conjugated polymers that simultaneously act as a light harvesting antenna and fluorescent resonance energy transfer (FRET

• and resulted in an increased fluorescence after several rounds of PCR [113]. Combination of single-labeled PNA probes with cationic conjugated polymers The absence of negative charges on the PNA backbone offers a unique advantage for the development of novel DNA assays that cannot be made with

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

• was observed. This resulted in an increase in the short circuit current from 1.63 mA/cm2 to 2.36 mA/cm2 with an increase in the overall efficiency by ≈46%. These studies suggest that planar-conjugated polymers based on flourene and benzothiadiazole (when substituted with appropriate groups) can play a

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

• Xiao Huang,
• Li Yang,
• Rikard Emanuelsson,
• Jonas Bergquist,
• Maria Strømme,
• Martin Sjödin and
• Adolf Gogoll

Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265

• polymers; polythiophene; Sonogashira coupling; thiophene; Introduction Currently organic conjugated polymers are attracting considerable interest for various applications in plastic electronics. In particular, poly(3,4-ethylenedioxythiophene) (PEDOT) [1] and its derivatives [2][3][4][5][6][7] play an

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

• p-type and n-type conjugated polymers or molecular materials (MM), have attracted significant attention as alternative solar cell technologies as they are light-weight, low-cost and offer the opportunity of cheaper manufacturing employing roll-to-roll printing processes [1][2][3]. Recent advances in

Comparing blends and blocks: Synthesis of partially fluorinated diblock polythiophene copolymers to investigate the thermal stability of optical and morphological properties

• Pierre Boufflet,
• Sebastian Wood,
• Jessica Wade,
• Zhuping Fei,
• Ji-Seon Kim and
• Martin Heeney

Beilstein J. Org. Chem. 2016, 12, 2150–2163, doi:10.3762/bjoc.12.205

• thin-film microstructure playing such a key role in the optoelectronic and charge transport properties of conjugated polymers, block copolymers naturally appear as useful tools for tailoring the thin-film morphology [1][2][3][4][5]. The propensity of some block copolymers to phase segregate at the nano

• conjugated polymers. In these polymerizations, such as Stille or Suzuki polycondensations, one approach to the block copolymer synthesis is the addition of a well-defined polymeric end-capper, commonly bromine terminated poly(3-hexylthiophene). An issue with this approach can be the formation of a mixture of

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• undiluted serum [82] a project that we are currently testing in human studies. I should point out that we have managed to marry the strenths of the polymer and fluorescent protein systems [83] using polymer–protein FRET to provide modulated output [84]. You'll remember that I said that conjugated polymers

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

• performance is presumably attributed to the limited solubility of the PTzBDT-1 in organic solvents resulting in enhanced aggregation and poor intermixing with the acceptor material in the active layer. Keywords: alkyl side chains; benzodithiophene; bulk heterojunction solar cells; 2D conjugated polymers

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

• Wei Li,
• Munechika Otsuka,
• Takehito Kato,
• Yang Wang,
• Takehiko Mori and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

• ]. Among them, the poly(triarylamine) derivatives are currently some of the best polymeric hole-transporting materials for the PSCs [13]. Carbazole (Cbz)-based conjugated polymers are widely used as active photo- and semiconducting materials in a variety of organic electronics due to their tunable optical

My maize and blue brick road to physical organic chemistry in materials

• Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

• creativity in (macro)molecular design and applied work with conjugated polymers. Tim pitched ideas for dozens of projects and let me decide where to focus. It took a few months and a few failed projects before I identified a clear research direction. In fact, one of those failed projects led to a new idea

• photobleaching, which is problematic for solid-state applications of conjugated polymers. Working with Tim I learned that new materials are interesting if they offer new properties, a lesson that still influences my research today. I learned how to manage my efforts, including when to stop working on

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• last decades, conjugated polymers (CPs) have been actively investigated as an alternative to conventional inorganic materials in many electronic applications due to their low cost and easy processability [1][2][3][4][5][6]. Among the various CPs, polyfluorenes (PFs) have been intensively studied as

• unique properties, and novel practical applications. The construction of polyrotaxane architectures has an impact on the polymer-chain behavior and subsequently generates smart functional polymeric materials [28][29][30][31]. Polyrotaxanes with conjugated polymers have attracted considerable attention

• conjugated polymers [16][17][18][19][20][26][27][28][29][30][31][32][33][34][35][36][37][38]. The first step in the preparation of conjugated polyrotaxanes is the threading of macrocyclic compounds (hosts) onto linear chains (guests), when a thermodynamically unstable inclusion complex (IC) is obtained. A

Life lessons

• Jonathan R. Nitschke

Beilstein J. Org. Chem. 2015, 11, 2350–2354, doi:10.3762/bjoc.11.256

• sixth – usually chloride – in its center [27]; Figure 2c illustrates a FeII12L12 pseudo-icosahedron with mer stereochemistry to its FeII centers, shown encapsulating B12F122− [28]. We also have a flourishing line of enquiry into conjugated polymers that are held together by metal-ion templation – the

A new approach to ferrocene derived alkenes via copper-catalyzed olefination

• Vasily M. Muzalevskiy,
• Aleksei V. Shastin,
• Alexandra D. Demidovich,
• Namiq G. Shikhaliev,
• Abel M. Magerramov,
• Victor N. Khrustalev,
• Rustem D. Rakhimov,
• Sergey Z. Vatsadze and
• Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2015, 11, 2072–2078, doi:10.3762/bjoc.11.223

• current values of oxidation at the iron atom. These findings allow us to state that the synthesized molecules are promising starting materials for the electrochemical synthesis of ferrocene-containing conjugated polymers. Conclusion In conclusion, a novel stereoselective route to ferrocenyl haloalkenes