Bis-naphthalimides bridged by electron acceptors: optical and self-assembly characteristics

Abstract

The self-assembly of small organic molecules into molecular stacks plays a vital role in the construction of stable supramolecular structures.

New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

“…1,8-Naphthalimide derivatives in OLEDs and OPVs have been studied as electron-transporting materials [ 23 , 24 ], emitters [ 25 , 26 , 27 , 28 , 29 , 30 , 31 ], emission polymers additionally transporting electrons [ 32 ], as a host in the guest-host structure (acting as a matrix for the blue emitter) [ 9 ], and as green dopant [ 33 ]. 1,8-Naphthalimides showed high electron mobility [ 34 ], and further the presence of a donor substituent allows to obtain compounds with dominant transport of holes and higher emission intensity [ 35 , 36 , 37 , 38 ] and high electron affinity [ 39 ]. Asymmetrical 1,8-naphthalimides structures, constructed from a single imide ring, are often tested as compounds substituted in the 4-C position for organic electronics [ 1 , 39 , 40 ].…”

“…In the Supplementary Information in Figure S1 (see ESI) the structures of bisnaphthalimide derivatives are presented, dividing them according to the type of linker between 1,8-naphthalimide unit and the core of the compound. The described bisnaphthalimide derivatives include symmetric donor-acceptor structures with linkers, such as, vinyl [ 47 ], ethynyl [ 36 ], azo- [ 39 , 48 ], imino- [ 45 ], C-S [ 49 ] or C-O [ 50 ] bonds as well as without linkers by directly C–C binding with aryl [ 38 , 51 ]. Moreover, the bisnaphthalimides described so far in their core contained the following derivatives: phenyl, carbazole, triphenylamine, thiophene or bitiophene ( Figure S1 ) [ 51 ].…”

Donor–acceptor–acceptor (D–A–A) type 1,8-naphthalimides as non-fullerene small molecule acceptors for bulk heterojunction solar cells

“…11 However the D–A systems based on NIs have a wide energy gap. 12 The electronic and photonic properties of the D–A NIs can be tuned by substitution at the C-4 or C-5 position.…”

“…The electron deficient 1,8-naphthalimide (NI) unit exhibits high electron affinity and high charge carrier mobility, and acts as an acceptor unit. 11 However the D–A systems based on NIs have a wide energy gap. 12 The electronic and photonic properties of the D–A NIs can be tuned by substitution at the C-4 or C-5 position.…”

Photophysics, Electrochemistry, Morphology, and Bioimaging Applications of New 1,8‐Naphthalimide Derivatives Containing Different Chromophores

“…Among the known acceptor chromophores, 1,8‐naphthalimides have gained much attention owing to their high electron affinity; optical, thermal, and chemical stabilities; promising electron‐transporting properties, and tunable fluorescent properties. A wide variety of organic dyes possessing the 1,8‐naphthalimide unit have found applications in organic light‐emitting diodes (OLEDs), organic solar cells (OSCs), and biological and chemical sensors .…”