Synthesis and characterization of 1,2,3,4-naphthalene and anthracene diimides

• Adam D. Bass,
• Daniela Castellanos,
• Xavier A. Calicdan and
• Dennis D. Cao

Beilstein J. Org. Chem. 2024, 20, 1767–1772, doi:10.3762/bjoc.20.155

• periphery of the aromatic core to yield different structural isomers is effective for producing interesting new materials. Ourselves and others have investigated 1,2,3,4-benzene diimide, also known as mellophanic diimide [1], as a building block for heteroacenes [2][3][4][5] and polyimides [6][7][8]. The

• organic thin-film transistors from heteroacenes. Inspired by these results, we sought to demonstrate the preparation of all-carbon scaffolds, i.e., acenes, that are cata-annulated with cyclic imides. Here, we communicate the successful synthesis of 1,2,3,4-NDIs and -ADIs and the characterization of their

• -delocalization. As part of our previous work constructing heteroacenes bearing cata-imide groups, we investigated the 9,10-diaza analog of compound 8-Hex (9, Figure 5). It is interesting to note that the all-carbon scaffold in 8-Hex results in a narrower bandgap than that of 9, with Δλmax = 85 nm. This

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• 73019, United States 10.3762/bjoc.20.92 Abstract Presented here is the design, synthesis, and study of a variety of novel hydrogen-bonding-capable π-conjugated N-heteroacenes, 1,4-dihydropyrazino[2,3-b]quinoxaline-2,3-diones (DPQDs). The DPQDs were accessed from the corresponding weakly hydrogen

• molecules; N-heteroacenes; hydrogen bonding; optoelectronic properties; organic field-effect transistors; organic semiconductors; Introduction The role of weak intermolecular interactions in tuning the properties of organic semiconductors has garnered significant attention in the past two decades, owing to

• and charge injection/extraction processes [7]. The additional merits of H-bonding designs in organic optoelectronic materials include higher thermal stability, synergistic stabilizing effects with π-stacking interactions, etc. [8]. Acenes and N-heteroacenes are two prominent π-conjugated scaffolds for

Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

• Mengjie Wang,
• Lanping Dang,
• Wan Xu,
• Zhiying Ma,
• Liuliu Shao,
• Guangxia Wang,
• Chunli Li and
• Hua Wang

Beilstein J. Org. Chem. 2022, 18, 809–817, doi:10.3762/bjoc.18.81

• the solid state mainly because such fused aromatic compounds often undergo increased Se–Se interactions, which confer ordering at the molecular scale and, thus, lead to well-aligned solid-state packing and excellent charge-transport properties [20][21]. However, as an important type of heteroacenes

• similar method, Takimiya reported the synthesis of six-ring-fused and four-ring-fused heteroacenes containing selenopheno[3,2-b]selenophene in 2007 and 2009, respectively [23][24]. Five years later, Cheng reported the synthesis of two types of five-ring-fused isomers of diselenopheno[2,3-b:7,6-b′]fluorene

• selenophene currently available, helicenes have received relatively little attention [27]. In our previous work, bull horn-shaped selenophene-based heteroacenes (1, Figure 1) and selenophene-based [7]helicene (2, Figure 1) were synthesized from the (TMS)2-substituted selenophene triacenes, 2,5-di

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

• Mio Matsumura,
• Takahiro Teramoto,
• Masato Kawakubo,
• Masatoshi Kawahata,
• Yuki Murata,
• Kentaro Yamaguchi,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2021, 17, 671–677, doi:10.3762/bjoc.17.56

• property; phosphorus; Introduction Phosphole-based heteroacenes are attracting increasing interest in various fields, such as organic synthesis, structural chemistry, and materials science [1][2][3][4]. The phosphorus atom of trivalent phosphorus compounds has a high chemical reactivity. Therefore, this

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

• systems. The various obtained heteroatom sequences ‘SSNS’ (SN4), ‘SNNS’ (SN4’’), and ‘NSSN’ (SN4’) allowed for evaluation of structure–property relationships relative to the sulfur analogue tetrathienoacene (‘SSSS’). In line with the results for the whole series of S,N-heteroacenes, we find that

• reaction; optoelectronic properties; S,N-heteroacene; structure–property relationship; Introduction Thienoacenes and related S,N-heteroacenes have been developed to important π-conjugated systems mainly for application as p-type semiconductor in organic electronic devices with excellent results [1][2][3

• ]. The series of thienoacenes consisting of only fused thiophene rings has been synthesized up to an octamer, whereby the longer members in the series quickly lose solubility [4][5][6]. The implementation of pyrrole rings into the fused ladder-type structure leads to the class of S,N-heteroacenes

Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction

• Nadezhda S. Demina,
• Nikita A. Kazin,
• Nikolay A. Rasputin,
• Roman A. Irgashev and
• Gennady L. Rusinov

Beilstein J. Org. Chem. 2019, 15, 2678–2683, doi:10.3762/bjoc.15.261

• used to architect various ring-fused S-heteroacenes, which have been studied extensively [8][9][10] due to their better characteristics compared to heteroatom-free acenes. For instance, S-heteroacenes have a better oxidation stability due to lower-lying HOMO levels, as well as more efficient charge

• -heteroacenes, which can limit the effectiveness of semiconducting films in the case of solution-processable electronics [11]. Introducing the NH-containing moieties, e.g., pyrrole rings, followed by attaching solubilizing substituents is one of the ways to solve this problem. Thus, different types of N,S

• -heteroacenes, including ones with TT-scaffold (Figure 1), which have promising electronic features, have been developed and are further investigated [12][13][14]. At present, the challenge is to develop effective ways of constructing the TT-based compounds, such as S- and N,S-heteroacenes, in order to

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

• ; heteroacene; selenophene; Introduction In recent years, great interest has been devoted to the development of new π-conjugated polycyclic molecules, in particular to polycyclic aromatic hydrocarbons (PAH) such as acenes [1], phenacenes [2], or nanographenes [3]. Corresponding heteroacenes incorporating

• heteroatoms such as nitrogen or sulfur represent encouraging alternatives to PAHs providing manageable electronic properties and increased chemical stability [4][5]. In this respect, series of heteroacenes consisting of fused five-membered heterocycles such as thienoacenes [6][7] or S,N-heteroacenes [8] were

• investigated and successfully used as building blocks for high-performance organic electronic materials and devices [9][10][11][12][13][14][15][16]. Among the different heteroatoms that can be introduced into heteroacenes and in contrast to corresponding thiophene-based systems, selenium (Se) has only

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives

• Mio Matsumura,
• Mizuki Yamada,
• Atsuya Muranaka,
• Misae Kanai,
• Naoki Kakusawa,
• Daisuke Hashizume,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

• corresponding phosphole derivatives with different electronic properties [10][11][12][13][14][15][16][17]. Phosphole-based ladder-type π-conjugated heteroacenes were shown to exhibit a high charge mobility and/or fluorescence quantum yields [18][19][20][21][22][23][24]. For example, dibenzo-fused phospholo[3,2

• -b]phosphole dioxides (Figure 1A) [25][26] and benzophosphole-fused tetracyclic heteroacenes, containing boron (B) [27][28][29], silicon (Si) [30], oxygen (O) [31], and sulfur (S) [32][33][34] (Figure 1B), were synthesized and their physical properties were studied. However, to the best of our

• knowledge, the synthesis of benzophosphole-fused indole derivatives as tetracyclic heteroacenes has not been reported. In 2015, Lu et al. reported the synthesis of only one phosphole and indole-fused pentacyclic heteroacene [35]. Recently, we reported simple and efficient synthetic routes to benzothiophene

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

• Roman A. Irgashev,
• Nikita A. Kazin,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136

• both nitro groups, unlike potassium salts of indole or carbazole, which have caused substitution of only one nitro group. Keywords: electrophilic aromatic substitution; indolo[3,2-b]carbazole; N-heteroacenes; nitration; nucleophilic aromatic substitution; Introduction Organic π-conjugated compounds

Syntheses of dibenzo[d,d']benzo[2,1-b:3,4-b']difuran derivatives and their application to organic field-effect transistors

• Minh Anh Truong and
• Koji Nakano

Beilstein J. Org. Chem. 2016, 12, 805–812, doi:10.3762/bjoc.12.79

• . Keywords: furan; heteroacenes; organic field-effect transistors; organic semiconductor; Introduction Organic semiconductors have significantly been developed in the past two decades by virtue of their advantages, such as low weight, flexibility, large-area processability, which are different features from

A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles

• Roman A. Irgashev,
• Arseny A. Karmatsky,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2015, 11, 1000–1007, doi:10.3762/bjoc.11.112

• thieno[3,2-b]pyrrole ring systems have been incorporated in the structures of various fused polycyclic compounds (heteroacenes), which have been used as efficient hole-transport materials for organic light emitting diodes (OLEDs) or field effect transistors (OFETs) [9][10][11][12][13][14][15]. Taking