Novel Highly Fluorescent Triphenylamine-Based Oligothiophenes^†

Abstract

A homologous series of novel amorphous oligothienyl-triphenylamines, comprised of head-to-tail coupled oligo(3-hexylthiophene)s covalently linked to a triphenylamine core, are disclosed. These hybrid systems, which differ by the length of the oligothiophene units from a monothiophene up to a quaterthiophene, were created via palladium-catalyzed cross-coupling reactions in good yields. The optical and electrochemical properties of these compounds were thoroughly investigated and are compared to the corresponding parent linear non-functionalized oligothiophenes, clearly demonstrating that these newly synthesized hybrid systems are characterized by outstanding absorption and emission properties. These molecules exhibit fluorescence quantum yields as high as 65%, which is unexpectedly high for thiophenebased materials. Based on this available data set, structure-property relationships were established, providing a deeper insight into the electronic nature of these materials and in this respect elucidating electronic differences between these star-shaped structures and their corresponding parent linear oligothiophenes.

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications

“…726 Cremer and Briehn reported oligothienyl-triphenylamines 5.21 (Chart 5.4), comprising head-to-tail coupled oligo(3-hexylthiophenes) as arms linked to a triphenylamine core. 727 The oligomers were built up Via Pd 0 -catalyzed cross-coupling reaction of a triphenylamine boronic ester and bromooligothiophenes in 70-75% yields. These oligomers showed strong absorption and emission transitions in the visible region with high fluorescence quantum yields reaching 65% for 5.21 (n ) 1).…”

Synthesis, Characterization and Properties of Novel Star‐Shaped π‐Conjugated Oligomers with Triphenylamine Core

“…On the other hand, the absorption of TPA-BT3 has a red shift compared with that of the star-shaped molecule in which the TPA core and the peripheral units are connected by single bonds. [13] Figure 2 shows the normalized UV-vis absorption and PL spectra of the four star-shaped oligomers in thin solid films. The relevant spectroscopic data are summarized in Table 1.…”

“…[7,11] Carbazole, triphenylamine, phenothiazine and bithiophene are four excellent hole-transporting chromophores. Their derivatives are often used as the hole-transporting materials for organic light-emitting diodes (OLEDs) [12,13] and organic solar cells (OSCs) [7,14] due to the good hole-transporting property, high charge mobility and high thermal stability. [10,15] Nevertheless, the electron-donating ability of these four hole-transporting chromophores are different, i.e.…”

The synthesis and optical properties of novel triphenylamine containing 1,3,4-oxadiazole derivatives

“…Triphenyl amine (TPA)-based polymers have a wide range of applications ranging from various opto-electronic applications to use as fluorescent sensors [1][2][3]. Poly (triphenylamine-p-phenylene vinylene) polymers with two different end groups have shown high fluorescence sensitivity towards o-nitrotoluene (o-NT) [4].…”