Imide-Modified Dinaphtho[1,2-b:2′,1′-d]thiophene and Dinaphtho[1,2-b:2′,1′-d]thiophene 13,13-Dioxide: Synthesis and Optoelectronic Properties

Abstract

Dinaphthothiophene has been reported as a promising p-type semiconductor. The development of high-performance n-type semiconductors is highly desirable. The introduction of an imide group into polycyclic aromatic hydrocarbons can lower their LUMO levels to meet the basic requirement of n-type organic semiconductor materials. In this work, we have synthesized four imide-modified dinaphthothiophenes and dinaphthothiophenedioxides. Their optoelectronic properties have been investigated. Their low-lying LUMO levels make them potential n-type semiconductor candidates.

Customizing Photoredox Properties of PXX‐based Dyes through Energy Level Rigid Shifts of Frontier Molecular Orbitals

“…Subsequent methylation with MeI gave 4 with an overall yield of 92 %. 5 was obtained in 49 % yield by a two‐step protocol including the in situ preparation of the boronate derivative from B 2 Pin 2 through Miyaura borylation reaction and subsequent Suzuki cross‐coupling with bromo‐derivative 4 in the presence of [Pd(dba) 2 ], SPhos, and Cs 2 CO 3 . Similarly, Suzuki cross‐coupling of methoxy‐naphthalenboronic acid with 4 gave 8 in 94 % yield .…”

Heteroacene Synthesis through C−S Cross‐Coupling/5‐endo‐digCyclization

“…These multiple C−S bond formations comprise the C−S cross coupling/cyclization sequence and the intramolecular double C−S cross‐coupling to generate the central thiophene ring. Common dibenzothiophene syntheses employ halide–lithium exchange or nucleophilic aromatic substitution at elevated temperatures . We used the [Pd(dba) 2 ]/DPPF catalyst earlier for the construction of dithienothiophenes, and now we applied these conditions to the cyclization reaction of 5 (Scheme , n =2).…”

Vertically π-Expanded Coumarins: The Synthesis and Optical Properties

“…The first attempt of bromination of phenol 3 with Br 2 or NBS caused the formation of a complex and inseparable product mixture. Eventually, phenol 3 was brominated in the presence of copper(I) bromide 22 and the resulting bromophenol 12 was subjected to tandem Suzuki reaction in the presence of bispinacoloborane 23 to obtain bis-phenol 15 in 21% yield (Scheme 4). The low yield of the last step can be associated with the presence of a free OH group.…”