Truxenone Triimide: Two‐Dimensional Molecular Arrangements of Triangular Molecules for Air Stable n‐Type Semiconductors

Abstract

cell membrane, [13,14] and in preparation of organic magnetic [15][16][17][18] and direduced materials. [19] Despite their intrinsic potential in the development of complementary circuits, non-fullerene n-type materials lag far behind compared to their counterpart p-type materials in terms of molecular diversity, air stability, and carrier mobility. [20,21] It has been realized that lowering the LUMO energy level of an n-type semiconductor increase the charge injection properties as well as enhances its stability towards air and moisture. [22,23] General design principle of high electron affinity organic materials involves the introduction of electron withdrawing imide groups onto π-conjugated periphery. Arylenediimides, especially pyromilliticdiimides (PMDI), [24] naphthalenediimides (NDIs) [25] and perylenediimides (PDIs) [26,27] (Figure 1a-c) and their derivatives are some of the well-studied n-type organic semiconductors prepared via introduction of electron withdrawing imide groups onto the periphery of p-type aromatic hydrocarbons. Furthermore, the solubility and the solid-state packing of the n-type semiconductors can be finely tuned by substitution on the nitrogen of the imide group.It is well established that incorporation of imide groups greatly enhances the electron-affinity of the parent materials, hence charge injection and transport properties. This suggests that planar π-conjugated templates that can support more imide groups insertion might help in improving the air stability and conductivity. [28] In addition, they allow multi-electron accumulation which has significant importance in both organic electronics and photonics [29,30] However, the reported protocols are mostly limited to diimidization of arylenes. and only a few examples of higher imides have been reported due to their synthetic complexity. [31,32] Again the symmetrical molecules having an odd-number of imide groups are rare and only a few C3-symmetric triimides such as mellitic triimide (MTI), [33] triphenylene triimide (TPTI), [34] decacyclene triimide (DTI), [28] hexaazatriphenylene triimide (HATTI), [35] and subphtaalocyanine triimide (SubPcTI) [36] are reported (Figure 1d-h).C3-symmetric molecules have fascinated scientists for their beauty [37] and crucial application in asymmetric catalysis, [37,38] molecular recognition, [37,39] discotic liquids, [40,41] and in electronic devices. [42] They can also lead to honeycomb superstructures. [43] Although, several C3-symmetric cores such as triphenylene (TP), [34,37,42] trinaphthaylene (TN), [34] hexaazatrinaphthyleneThe preparation of a new class of electron deficient organic compounds is of great interest for the development of high-performance n-type organic semiconductors. Herein, the facile synthetic protocol for the isolation of the first examples of truxenone triimide (TTI) is reported. The electrochemical analysis of the resulting TTIs confirms that the multi-imidization helps in lowering the LUMO energy level, tailoring prerequisite optoelectronic and/ or semiconducting prope...

Naphthalimide-based conjugated macrocycles possessing tunable self-assembly and supramolecular binding behaviours

“…Among them, the host-guest interaction refers to the process in which two or more kinds of molecules, namely the host and the guest molecule, are combined by non-covalent bonds ( Yang et al, 2015 ; Li et al, 2020 ), while self-assembly is the process in which molecules or parts of molecules form ordered aggregates spontaneously ( Zhou and Yan, 2009 ; Song et al, 2021 ). These supramolecular complexes formed by non-covalent interactions can realize molecular recognition, catalysis, reaction, transfer and other functions ( Park and Simmons, 1968 ; Kim et al, 2019 ; Dey et al, 2021 ) ( Ghosh et al, 2018 ) ( Ghosh et al, 2022 ) ( Kumar et al, 2022 ), which have important theoretical significance and broad application prospects in materials science, information science and life science. We pay special attention to the supramolecular properties of p -conjugate system.…”