An unusual self-assembling columnar mesogen prepared by tethering a planar naphthalenediimide acceptor to bent phenothiazine donors

Abstract

Tethering of two shape mismatched donors and acceptor leads to an unusual mesogen design.

Columnar liquid-crystalline J-aggregates based on N-core-substituted naphthalene diimides

“…Even though NDI-based supramolecular polymers have been widely investigated, it is somehow surprising the scarce examples of NDI liquid crystals existing in bibliography, 33–41 especially compared to its larger parent perylene diimides (PDIs). 42–48 Different molecular designs have been applied to develop liquid-crystalline (LC) NDIs, as for example, using perfluorinated 34,35 or oligodimethylsiloxane lateral chains, 41 amphiphilic systems, 36 or donor–acceptor dyads, 39,40 while the introduction of H-bonding units in the NDI design has been scarcely explored. 33 In all these examples, the NDIs are functionalized with alkyl groups at the imide positions and organize in columnar assemblies by the common co-facial π–π stacking.…”

Liquid-Crystalline Naphthalene and Perylene Bisimides with a D2–π2–A Architecture for High-Mobility Organic Field-Effect Transistors

“…However, it must be noted that most of the columnar semiconductors are acceptable hole carrier materials (p-type), and there is a dearth of good electron carrier materials (n-type). − Col LC-derived NDI, − PBI, , and their derivatives bring together favorable absorption properties, electron-transport behavior, and 1D columnar self-assembly, thus making them highly attractive for application in organic electronics. , The imidazole moiety is an electron-deficient moiety that can be used for hydrogen bond formation due to the presence of free −NH and thus plays a significant role in the creation of supramolecular aggregates. Further, this −NH can be subjected to N -alkylation to modify the solubility and self-assembly.…”

“…The solution-processed bottom gate–top contact organic field-effect transistors (OFETs) showed an excellent hole mobility of 0.70 cm 2 /V·s with an on/off ratio of 10 7 . Considering all of the above points, we envisaged the synthesis of a new class of self-assembling organic semiconductors comprising a tetrasubstituted imidazole moiety bearing two di-alkoxy phenyl units as electron donors (D), − central naphthalene/perylene bisimide moieties as acceptor (A) units, and phenyl moieties as π-bridges between the D and A units . The structures of the final target molecules based on the proposed donor−π–acceptor−π–donor (D 2 –π 2 –A) architecture are shown in Figure .…”