Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• under light activation thus prompted the investigation of 1,2-dithia-3,5-cyclohexadienes as synthetic photoprecursors of thiophene-based π-CPCs. In this sense, Schroth et al. reported the synthesis of thienothiophene and benzothienothiophene 40 from dithiin key intermediates (Scheme 11, top) [71]. Benzo

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• absorption. A solution-processed OLED was fabricated using low turn-on voltage, which had performances with maximum power, current, and external quantum efficiencies of 6.70 lm/W, 10.6 cd/A, and 4.61%, respectively. Keywords: OLED; organoboron; solution processes; thienothiophene; triphenylamine

• properties indicated that the composition of thienothiophene, triphenylamine, and boron is a highly suitable combination for fluorescent organic electronics in display technology. Experimental General methods 1H and 13C NMR spectra were recorded on a Varian model NMR spectrometer (500 and 126 MHz) and

• ]. Synthesis of 7 Synthesized as described in [23]. To a mixture of thienothiophene 4 (250 mg, 0.770 mmol) and borolane 6 (320 mg, 0.845 mmol) dissolved in THF (25 mL) and degassed for 45 min with N2 was added K2CO3 (2.5 mL, 2.5 M) and Pd(PPh3)4 (0.077 mmol). The mixture was then saturated with N2, the

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

• polymers in the design of flexible OSCs. Condensed thienothiophene substituents can also be used as the donor component of the monomeric isoindigo unit (Scheme 17). The first data on the use of these compounds as donor components of OSCs (mixed with PC61BM) showed that the technology of preparing a thin

Synthesis and characterization of S,N-heterotetracenes

• Astrid Vogt,
• Florian Henne,
• Christoph Wetzel,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2020, 16, 2636–2644, doi:10.3762/bjoc.16.214

• -dibromothienothiophene 2 [39], which was obtained from thieno[3,2-b]thiophene (1) [38], was triisopropylsilyl (TIPS)-protected by lithium-halogen exchange with n-BuLi and triisopropylsilyl chloride to give thienothiophene 3 in 69% yield. A halogen dance reaction of 3, induced by lithium diisopropylamide (LDA) at −78 °C

• , gave the corresponding β-brominated thienothiophene 4 in 91% yield [6]. Compound 4 was selectively brominated in α-position by using NBS in DMF at room temperature to give dibrominated thienothiophene 5 in 92% yield which was coupled in a Negishi-type cross-coupling reaction with zincated 2,3

• the azide route. The synthesis started from the above mentioned brominated thieno[3,2-b]thiophene 3, which was coupled with zincated 2,3-dibromothiophene 6 in a Negishi-type cross-coupling reaction with Pd(dppf)Cl2 as catalyst to give thiophene-substituted thienothiophene 10 in 72% yield. In the next

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

• significant role in increasing the efficiency for OPVs [30][31]. However, fused π-bridges (such as thienothiophene) having a larger molecular structure and higher degree of conjugation are less explored with respect to thiophene and furan spacers. Thienothiophene ensures a highly delocalized electron system

• and higher charge carrier mobility due to its rigid and coplanar fused structure. Also, some thienothiophene-based polymers show a noticeable bathochromic shift in their absorption spectra in comparison with thiophene-substituted polymers [32][33][34]. Herein, keeping all these criteria in mind, we

• , the effect of planarity and conjugation extension on the polymer backbone was also studied by coupling with a fused thienothiophene moiety. Results and Discussion For the synthesis of polymers with alternating donor–acceptor–donor architecture, suitable monomers were first prepared (Scheme 1). The

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

• ], thienyl group [16][17][18], and thienothiophene [17][19]. Structure modifications of the BDT core with aromatic units extend the π-conjugation of BDT unit to a two-dimensional structure, which increases intermolecular interactions, and consequently improves the device performance. The other one is to

The chemistry of bisallenes

• Henning Hopf and
• Georgios Markopoulos

Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225

[3.3]Dithia-bridged cyclophanes featuring a thienothiophene ring: synthesis, structures and conformational analysis

• Sabir H. Mashraqui,
• Yogesh Sanghvikar,
• Shailesh Ghadhigaonkar,
• Sukeerthi Kumar,
• Auke Meetsma and
• Elise Trân Huu Dâu

Beilstein J. Org. Chem. 2009, 5, No. 74, doi:10.3762/bjoc.5.74

• ], nonlinear optics [22] and axially chiral systems [23]. We have also recently incorporated a thienothiophene ring within the cyclophane framework via its 3,4-positions, leading to the synthesis of meta type 1,3-dithia-bridged thienothiophenophanes 1–2 [24]. Cyclophanes 1–2 (Figure 1) have been found to

• exhibit thia-bridge inversion down to −50 °C with an estimated energy barrier >25 kJ mol−1. In the present work, we deemed it of interest to exploit the other available positions of the thienothiophene ring, namely the 2, 5 positions to access a new set of bridged [3.3]dithia-thienothiophenophanes 7, 9

• construct cyclophanes 7, 9 and 11 was prepared as outlined in Scheme 1. The starting material, thienothiophene diester 3 was readily prepared in multigram quantities by a modification of our procedure [25]. Reduction of 3 with LiAlH4 in dry THF, followed by basic aqueous work-up gave diol 4 in 91% yield

The efficient synthesis of dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene and cyclopenta[1,2-b:4,3-b′]bis(benzo[d]thiophen)-6-one

• Zhihua Wang,
• Sheng Zhu,
• Jianwu Shi and
• Hua Wang

Beilstein J. Org. Chem. 2009, 5, No. 55, doi:10.3762/bjoc.5.55

• nm and 380 nm. Both 1 and 2 possess molecular connectivities of cross-conjugated π-system that shows π-electron delocalization with helical distortion. Conclusion Derivatives of benzothiophene, thienothiophene, and thienodithiophene with good characteristics for OFETs were recently reported [5][6][7