Columnar Mesomorphism of Board‐Shaped Perylene, Diketopyrrolopyrrole, Isoindigo, Indigo, and Quinoxalino‐Phenanthrophenazine Dyes

Abstract

The properties of organic dyes depend as much on their intermolecular interactions as on their molecular structure. While it is generally predictable what supramolecular structure would be ideal for a specific application, the generation of specific supramolecular structures by molecular design and suitable processing methods remains to be a challenge. A versatile approach to different supramolecular structures has been the application of mesomorphism in conjunction with alignment techniques and self‐assembly at interfaces. Reviewed here is the columnar mesomorphism of board‐shaped dyes perylene, indigo, isoindigo, diketopyrrolopyrrole, and quinoxalinophenanthrophenazine. They generate a larger number of different supramolecular structures than conventional disc‐shaped (discotic) mesogens because of their non‐circular shape and directional intermolecular interactions. The mesomorphism of all but the perylene derivatives is systematically and comprehensively covered for the first time.

Recent advances in the application of isoindigo derivatives in materials chemistry

“…Since the pioneering works on the use of isoindigo derivatives in the design of OSCs [3][4][5], specialists in this field have made significant progress in tuning and improving their properties [6][7][8][9][10][11][12]. The main photophysical characteristics that determine the effectiveness of OSCs are open circuit voltage (V OC ), shortcircuit current (J SC ) and fill factor (FF).…”

Pyrene-Fused Poly-Aromatic Regioisomers: Synthesis, Columnar Mesomorphism, and Optical Properties

“…Of particular interest in this field of research are discotic liquid crystals (DLCs), which usually form columnar nanostructures through self-assembly, and as such represent a unique type of soft material with anisotropic one-dimensional electrical and photoconductive properties [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 ]. DLCs display higher charge-carrier mobility when compared with that of amorphous silicon, π-conjugated polymers, and polydomain crystalline materials [ 18 ], with advantageous features of easier processing into thin-film electronic devices [ 10 ].…”

Synthesis, self-assembly and optical properties of some rigid π-bridged triphenylene dimers

“…Although the emergence of liquid crystalline phases is quite easily guaranteed by adapted molecular design, some specific geometrical considerations and the association of various molecular species between them make it difficult to predict the types of organizations, as well as their stability and resilience towards thermal/optical/chemical stresses or the characteristics of their intrinsic physical properties. 25 By using the versatile synthetic methods mentioned earlier, a great diversity of p-conjugated heterocyclic molecules has thus emerged, with molecules having cross-, [26][27][28][29][30][31] board- [32][33][34] and butterfly-like 35,36 shapes, integrating various types of electroactive molecular units within their structure such as fluorene, 36 fluorenone, [36][37][38] carbazole, 36 benzothienobenzothiophene, 39,40 or other fused-thiophene [41][42][43][44][45][46][47][48][49][50] building blocks. These systems show, as expected by design, mainly columnar mesophases with high thermal stability, as well as, depending on their intrinsic molecular structure, interesting photoluminescence, solvent gelation ability and/or charge carrier mobilities, of relevance for electronics-based applications.…”