Synthesis and properties of perfluoroalkylated TIPS-pentacenes

Electroactive Dyes Based on 1,8‐Naphthalimide with Acetylene Linkers as Promising OLED Materials – the Relationship Between Structure and Photophysical Properties

“…The highest percentage of residual weight (CR) was also observed for this derivative (44 %). The other compounds at 800 °C also do not decompose completely, which is typical for molecules with an extended aromatic structure [49,50] . In the first heating scan (during DSC measurements), an endothermic peak was seen for the compounds NI1 ‐ NI3 , corresponding to the melting points (236–294 °C).…”

“…The other compounds at 800 °C also do not decompose completely, which is typical for molecules with an extended aromatic structure. [49,50] In the first heating scan (during DSC measurements), an endothermic peak was seen for the compounds NI1-NI3, corresponding to the melting points (236-294 °C). In the following cooling scan, no peaks due to crystallisation appeared for the samples.…”

Tetra(peri‐naphthylene)anthracene: A Near‐IR Fluorophore with Four‐Stage Amphoteric Redox Properties

“…[11] Furthermore, cyclopentannulation of acenes resulted in polycyclic scaffolds with increased electron affinity and stability. [8,12] For example, cyclopenta[hi]aceanthrylene (4) with its low-lying lowest unoccupied molecular orbital (LUMO) was successfully implemented upon appropriate functionalization as an electron acceptor component in organic semiconductors. [8a,b,13] Decacyclene (5) with its three cyclopentadiene moieties and 36 sp 2 carbons represents an electron deficient fragment of C 60 prone to four reversible reduction steps.…”

“…Within the ongoing quest for novel technologically relevant electron acceptors several approaches have been established [1] . Among these approaches the decoration of the inherently electron‐rich polycyclic aromatic hydrocarbons (PAHs) with electron‐withdrawing moieties, such as cyano, [2] fluoro, [3] perfluoroalkyl, [4] and imide moieties [3,5] is certainly the most straightforward one. Nevertheless, next to the desired electron affinity increase these functionalities may lead to stability issues due to their inherent reactivity, which is detrimental for the use of such compounds as electron‐transport materials in organic electronics [1b,6] .…”

Tetrafluoroethylation of Electron‐Rich Alkenyl Iodides Enabled by in situ Generation of Solvent‐Stabilized “Ligandless” CuCF2CF2H

“…To comparatively determine the performance of our system, we then explored alternative protocols that could potentially generate the solvent-stabilized "ligandless" complex CuCF 2 CF 2 H (Table 2, entries 3, 4). Preliminary attempts to generate CuCF 2 CF 2 H in situ from Cu(0) [16] and commercially available 1,1,2,2tetrafluoroethyl iodide 4, followed by its reaction with model iodobenzene in dry/degassed DMF, afforded the corresponding 1,1,2,2-tetrafluoroethylbenzene [17] in a 65% yield (SI, Figure S5). However, this Ullmann-type reaction required harsh conditions (130 °C, 19 h) that may not be suitable for 2-iodo-D-glycals, which are sensitive substrates.…”