Asymmetric pyrene derivatives for organic field-effect transistors

Abstract

For the synthesis of an ortho-dithienylpyrene, a K-region bromination of pyrene was developed which enabled the first reported, non-statistical asymmetric functionalization of pyrene at the 4, 5, 9 and 10 positions. Crystal structures, optical and electronic properties and FET characteristics have been investigated.

Blue-Emitting Butterfly-Shaped 1,3,5,9-Tetraarylpyrenes: Synthesis, Crystal Structures, and Photophysical Properties

“…al. 10 have developed an asymmetric functionalization method to direct bromine atoms to the K-region without the need for tert-butyl groups. Additionally, in our laboratory, we also reported the selective formation of the 5-mono-and 5,9-di-substitution products from 7-tert-butyl-1,3-dimethylpyrene by formylation and acetylation depending on the type of Lewis acid catalyst deployed.…”

Synthesis, characterization and optical properties of novel oligothiophenes bearing pyrene units attached via well defined oligo(ethylene glycol) spacers

“…On the other hand, we achieved the synthesis of the oxoborolanes [2,5-bisoxoborolanethiophene (10) and 5,5 0 -bisoxoborolane-2,2 0 -bithiophene (11)]. First, we prepared the brominated compounds 2,5-dibromothiophene and 5,5 0 -dibromo-2,2 0 -bithiophene, using NBS as a source of bromine.…”

“…227-231 C). (11). First 5,5 0 -dibromo-2,2 0 -bithiophene was synthesized, using a bromination procedure similar to that described for the previous compound.…”

“…It is very well known that p-conjugated oligomers are considered as promising materials since their optical and electrical properties make them excellent prospects for the elaboration of optoelectronic devices such as OFETs [11], OLEDs [12], electrooptic modulators and photovoltaic cells [13]. In oligothiophenes, the high conjugation degree causes a red-shift of the absorption and emission transition bands to the visible range, a significant reduction of the oxidation potentials as well as a high stabilization of the resulting radical-cation species, which is helpful for the elaboration of electronic materials [14].…”

4,5‐Pyrenocyanine—Just Another Phthalocyanine? A STM and 2D WAXS Study

“…[17] Recently, we reported that the treatment of compound 2 with N-bromosuccinimide (NBS) in concentrated sulfuric acid at room temperature gives 4,5-dibromo-9,10-diketopyrene 3 in quantitative yield. [18] This key step opens the way to a whole series of 4,5-versus 9,10-substituted pyrene derivatives. As our interest lies in the introduction of solubilizing groups, reductive alkylation was achieved using alkyl bromides in the presence of sodium dithionite.…”