Ditriphenylenothiophene butterfly-shape liquid crystals. The influence of polyarene core topology on self-organization, fluorescence and photoconductivity

Abstract

Two series of regio-isomeric butterfly-shape liquid crystalline systems, based on a ditriphenylenothiophene core (/-DTPT) equipped with eight peripheral long alkoxy chains, were synthesized in two steps by the Suzuki-Miyaura cross-coupling/Scholl...

2-Aryl-1,3,4-trifluoro-6,7,10,11-tetrakis(alkoxy)triphenylene: a remarkable and highly inclusive mesomorphic platform

“…For direct comparison of the impact of fluorine atoms on the mesomorphism and the role of arene-fluoroarene interactions in mesophase stabilization, a nonfluorine homologue, namely 2,3,6,7-tetrakis(hexyloxy)-10-phenyltriphenylene (BTP6), was also synthesized by the Pd-catalyzed Suzuki-Miyaura cross-coupling and FeCl 3 Scholl intramolecular tandem oxidative cyclization reactions (Scheme S4, ESI †). [14][15][16][17][18][19] Prior to the preparation of the functional set of arylsubstituted triphenylene derivatives, 2Li-BP8 was first reacted Scheme 1 Synthesis, molecular structures, nomenclature and yields of 2-aryl-1,3,4-trifluorotriphenylenes.…”

“…The synthesis of most polycyclic aromatic discogens is mainly based on transition metal catalyzed-based reactions such as Suzuki-Miyaura, Heck, Sonogashira cross-couplings and oxidative p-extended Scholl reactions. [14][15][16][17][18][19] Triphenylene derivatives are overwhelming in DLCs, 20 and the archetypical representative, i.e. 2,3,6,7,10,11-hexakis(alkoxy)triphenylenes, can be simply prepared on a large scale in one step by the highly efficient oxidative trimerization of 1,2-dialkoxybenzene catalyzed by FeCl 3 in MeOH.…”

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

“…They were found to self-assemble into columnar mesophases with hexagonal and rectangular symmetry (depending on the nature of the chains R and R′), the non-centrosymmetric diimides 7 having much larger mesophase ranges than their centrosymmetric counterparts, 8 . Recently, our groups have successfully applied the combination of Suzuki cross-coupling [ 61 ] and Scholl reaction [ 62 ] in tandem together for the construction of various new π-extended aromatic DLC systems, based on triphenylene [ 63 , 64 ], thiophene and fused thiophene [ 65 , 66 , 67 , 68 ], benzothienobenzothiophene (BTBT) [ 69 ], carbazole [ 70 ], fluorene [ 70 ], dibenzothiophene [ 71 ], naphthalene [ 72 ], and pyridine [ 73 ].…”

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.…”