Diseleno[2,3-b:3′,2′-d]selenophene and Diseleno[2,3-b:3′,2′-d] thiophene: Building Blocks for the Construction of [7]Helicenes

Abstract

New building blocks, 2,5-di(trimethylsilanyl)diseleno[2,3-b:3',2'-d]selenophene ((TMS)-DSS) and 2,5-di(trimethylsilanyl)diseleno[2,3-b:3',2'-d]thiophene ((TMS)-DST), for helicenes were obtained from selenophene with total yields of 54 and 61%. From (TMS)-DSS and (TMS)-DST, selenophene-based hetero[7]helicenes, 5,5'-di(trimethylsilanyl)benzo[1,2-b:3,4-b']bis(diseleno[2,3-b:3',2'-d]thiophene) (rac-1), and 5,5'-di(trimethylsilanyl)benzo[1,2-b:3,4-b']bis(diseleno[2,3-b:3',2'-d]selenophene) (rac-2) were prepared. The overall yields from selenophene were approximately 6.5 and 6.1%, respectively. Intermolecular interactions such as C-Se, C-S, and Se-Se were observed in the crystal packings of rac-1 and rac-2. In addition, the absorption behaviors of rac-1 and rac-2 were investigated.

Bichalcogenophene Imide-Based Homopolymers: Chalcogen-Atom Effects on the Optoelectronic Property and Device Performance in Organic Thin-Film Transistors

“…For the synthesis of the new dibrominated monomer BSeI-Br (Scheme 1b), bromoselenophene 5 was first obtained by treating selenophene with N-bromosuccinimide (NBS), 71 which was then lithiated with n-BuLi and quenched by chlorotrimethylsilane (TMSCl) to afford compound 6 with an excellent yield of 94%. 71,72 The key for the synthesis of 7 is the base-catalyzed halogen dance reaction using selenophene with bromine at one α-position and with another α-position protected by the TMS group.…”

“…For the synthesis of the new dibrominated monomer BSeI-Br (Scheme b), bromoselenophene 5 was first obtained by treating selenophene with N -bromosuccinimide (NBS), which was then lithiated with n -BuLi and quenched by chlorotrimethylsilane (TMSCl) to afford compound 6 with an excellent yield of 94%. , The key for the synthesis of 7 is the base-catalyzed halogen dance reaction using selenophene with bromine at one α-position and with another α-position protected by the TMS group . The TMS-protected 7 was subjected to lithiation followed by quenching with dry carbon dioxide to give the key dicarboxylic acid 8 in a yield of 64%, which was then converted to dibrominated 9 using the NBS as the brominating agent with a yield of 87%.…”

Symmetric Mixed Sulfur–Selenium Fused Ring Systems as Potential Materials for Organic Field‐Effect Transistors

“…However, owing to a lack of available starting materials, up to now the development of reliable synthetic pathways toward seleniumbased materials is matter of ongoing research. [21][22][23] Herein, we report on the design and synthesis of regioisomeric chalcogenopheno [1]benzochalcogenophene (CBC) building blocks. These selenium-based moieties were applied in a series of symmetrical ene-linked p-conjugated organic semiconductors, which were characterized by NMR, UV/Vis absorption spectroscopy, cyclic voltammetry and X-ray diffraction (XRD).…”

“…Thus, selenophene‐fused aromatics constitute attractive candidates for electronic applications. However, owing to a lack of available starting materials, up to now the development of reliable synthetic pathways toward selenium‐based materials is matter of ongoing research [21–23] …”

Recent Advances in the Syntheses of Helicene-Based Molecular Nanocarbons via the Scholl Reaction

“…由 n 个邻位稠合苯环构成的分 子称为[n]螺烯. 若分子骨架中含有杂原子(如氮、 氧、 硼、 硫、磷等), 并产生邻位稠合的螺旋型结构, 则被称为杂 螺烯 [19][20][21][22][23][24][25] .…”