Strategien für die Synthese funktioneller Naphthalindiimide

Abstract

Naphthalindiimide, die lange im Schatten ihrer größeren homologen Perylendiimide standen, gehören gegenwärtig zu einer der am meisten untersuchten organischen Substanzklassen. Zu verdanken ist dies vornehmlich den präparativen Vorarbeiten zur Kernfunktionalisierung zu Beginn des letzten Jahrzehnts, welche die vielfältigen strukturellen Modifizierungen des Naphthalindiimid‐Grundkörpers ermöglichten. Mit relativ geringem Syntheseaufwand sind Verbindungen mit stark veränderten optischen und elektrochemischen Eigenschaften zugänglich, die je nach Funktionalisierung leicht und effektiv eingestellt werden können. Dies hat verschiedene interessante Anwendungen zur Folge. So macht der elektronenarme Charakter der Verbindungen sie besonders auf dem Gebiet der organischen Elektronik als luftstabile n‐Halbleiter höchst bedeutsam, während die durch Kernsubstituenten über den gesamten sichtbaren Spektralbereich einstellbaren Absorptionsbanden interessante Photosysteme und Photovoltaikanwendungen möglich gemacht haben. Dieser Aufsatz gibt einen Überblick über die verschiedenen Möglichkeiten zur Kernfunktionalisierung und die vornehmlich in den letzten fünf Jahren entwickelten Synthesestrategien zur Kernexpansion des Naphthalindiimids.

9H‐Quinolino[3,2,1‐k]phenothiazine: A New Electron‐Rich Fragment for Organic Electronics

“…The electron-rich character of the QPTZ fragment is the most important feature and has been investigated by cyclic (Figure 2). In oxidation, the two compounds remarkably present two reversible single-electron oxidation processes with peak potentials E 1 /E 2 (versus SCE) recorded at 0.89/ 1.61 Vf or SQPTZ-F and at 1.0/1.64Vfor SQPTZ-TXO 2 .A sT XO 2 and Fm oieties are oxidised through irreversible processes, these two oxidation waves have been assigned to two singleelectron transfers involvingt he QPTZ core. Thus, the first oxidation of the QPTZ fragment remarkably occurs at al ess anodic potentialt han that of the PA (E 1 > 1.11V in SPA-TXO 2 ) [17] and that of the IA core (E 1 = 1.33 Vf or SIA-TXO 2 and 1.19 Vf or SIA-F).…”

“…Over the last 30 years,t he fantastic emergence of organic electronics is assignable to the design,t he synthesis and the study of thousands of organic semiconductors (OSCs) with specific properties fitting with the different electronic devices. [1][2][3][4] Since the discoveryo ft he "host/guest concept" in phosphorescent organic light-emitting diodes (PhOLEDs), [5] the designo fO SCs usable as host materials for blue-emitting phosphors has been an intense research field worldwide. [4] In addition to its high thermal/morphological stabilitya nd its high triplet energy (E T ), an ideal host should also possess ab ipolar character,w ith HOMO and LUMO energy levels adapted to the Fermi levels of the electrodes.…”

Naphthalenediimide – A Unique Motif in Macrocyclic and Interlocked Supramolecular Structures

“…N,N ‐Functionalized NDI derivatives are readily accessible by treatment of 1,4,5,8‐naphthalenetetracarboxylic acid dianhydride (NDA) with aliphatic or aromatic amines, in polar solvents such as DMF or N , N ‐dimethylacetamide, at high temperatures . Simple NDI chromophores display intense absorption bands, in DCM, at wavelengths lower than 400 nm, and weak emission bands, with short Stokes shifts and low quantum yields.…”

Improved Transistor Performance by Modulating Molecular Packing with Donor and Acceptor Moieties

“…[1,[5][6][7] The strong electrostatic interactions deriving from the donor and acceptorm oieties can be expected to tune the molecular packing, enhance the intermolecular charge transport and increase the carrierm obilities. [2,8] However,aclear relationship betweenthe D-A interaction and molecular packing is few reported yet.Over the years, severalf amous molecular blocks,s uch as benzothiadiazole (BT), [9,10] naphthalene tetracarboxylic diimide (NDI), [11][12][13] diketopyrrolopyrrole (DPP), [14][15][16] benzodifurandionebased oligo(p-phenylene vinylene) (BDOPV) have been designed synthesized forh igh-performance semiconductors for opticala nd electronic applications. BDOPV have been explored as an excellent block for OFET, [17,18] organic thermoelectric (OTE), [19,20] andn ear-infrared (NIR)l ight applications.…”

“…Over the years, severalf amous molecular blocks,s uch as benzothiadiazole (BT), [9,10] naphthalene tetracarboxylic diimide (NDI), [11][12][13] diketopyrrolopyrrole (DPP), [14][15][16] benzodifurandionebased oligo(p-phenylene vinylene) (BDOPV) have been designed synthesized forh igh-performance semiconductors for opticala nd electronic applications. BDOPV have been explored as an excellent block for OFET, [17,18] organic thermoelectric (OTE), [19,20] andn ear-infrared (NIR)l ight applications.…”