Substituted triphenylamines as building blocks for star shaped organic electronic materials

Abstract

A series of star shaped organic semiconductors was synthesized and characterized. The applicability of these materials in organic electronic devices was demonstrated.

Triphenylamine–Thienothiophene Organic Charge‐Transport Molecular Materials: Effect of Substitution Pattern on their Thermal, Photoelectrochemical, and Photovoltaic Properties

“…Our synthetic route to the target molecules is shown in Figure . Both compounds were prepared in a single step in excellent yields by employing a two‐fold Suzuki cross‐coupling reaction between dibromothieno[3,2‐b]thiophene and 4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)‐ N , N ‐bis(4‐methoxyphenyl)aniline . The structures of both compounds were determined by using 1 H and 13 C NMR spectroscopy and HRMS.…”

Color Fine‐Tuning of Optical Materials Through Rational Design

“…The building blocks incorporated in the substances under investigation are thiophenes used as linkers and TPA units serving as caps. Alteration of the molecular design of triphenylamine‐based materials by introducing either electron‐donating or ‐withdrawing substituents allows fine tuning of photophysical properties of a variety of fluorescent materials . Also the application of planarized or deplanarized moieties strongly influences absorption and emission characteristics .…”

“…The synthetic linkage of triphenylamines (TPA), indolocarbazole (ICz) as well as phenylcarbazole (PCz) scaffolds and thiophene‐based linkers toward symmetrical bis(triarylamines) was realized by Suzuki cross‐coupling reaction. A general procedure developed in an earlier study tolerating a broad spectrum of functionalized TPA boronic acid esters was applied for the synthesis of BoMA‐1T , BHA‐2T , BpMA‐2T , BMOA‐2T , BFA‐2T , BoMA‐2T , PCz‐2T , ICz‐2T , BHA‐3T , BpMA‐3T , BMOA‐3T , BFA‐3T , BHA‐4T , BpMA‐4T , BMOA‐4T , BFA‐4T , BHA‐TT , BoMA‐TT , PCz‐TT , ICz‐TT , BHA‐DTT , BoMA‐DTT , PCz‐DTT , ICz‐DTT , PCz‐1T and ICz‐1T . A convenient synthetic pathway for planarized TPA moieties PCz and ICz was previously described .…”

“…Linker precursors including 2,5‐dibrominated thiophene‐, bi‐, ter‐ and quaterthiophenes 1T‐4T were synthesized according to literature, while fused thiophene derivatives TT and DTT were obtained by a procedure as described by Frey . The synthesis of the required TPA boronic ester derivatives of BHA, BpMA, MOA, BFA, BMSO2A and BCNA for Suzuki cross‐coupling was also described previously by our group . All efforts to produce sterically hindered derivative BoMA via the same classical methods (eg.…”

“…For this reason a common approach is to combine these thiophenes with modified triphenylamine (TPA) scaffolds, which are frequently used in OE due to their beneficial electron donor and hole transport properties . The materials under investigation combine these structural scaffolds consisting of thiophene based linker systems and triarylamine containing cap units (Figure ), thus leading to a material class featuring good charge carrier mobilities originating from the oligothiophene unit and improved fluorescent properties by preventing self‐quenching caused by the introduction of the TPA motifs . Each individual building block can readily be synthesized or structurally modified to meet electronic and spectroscopic requirements.…”