Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• chains and derived from the classical triphenylene core self-assembling in columnar mesophases based on this paradigm. These mesogenic compounds were simply obtained in good yields by the nucleophilic substitution (SNFAr) of various types of commercially available fluoroarenes with the electrophilic

• emergence of a more ordered, 3D phase for some PHn derivatives observed on cooling at lower temperature. As expected, neither F or BTP6 are mesomorphic. As for the larger fluorine derivatives Gnm (G55, G66, and G48), they all possess enantiotropic columnar mesophases right from room temperature up to 183

• Fn and dimers Gnm display Colhex and Colrec mesophases, respectively, with high stability of the columnar mesophases due to strong arene–perfluoroarene polar π-interactions and related stereoelectronic effects. These Janus-type Fn compounds exhibit high clearing temperatures, and no crystalline phase

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• understanding charge transport in columnar mesophases [9][10][11][12][13][14]. High charge carrier mobilities of 1.1 cm2 V−1 s−1 for p-type and up to 6.0 cm2 V−1 s−1 for n-type liquid-crystalline semiconductors have already been reported [15]. Among the various discotic liquid crystal materials, perylene

Triphenylene discotic liquid crystal trimers synthesized by Co₂(CO)₈-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition

• Bin Han,
• Ping Hu,
• Bi-Qin Wang,
• Carl Redshaw and
• Ke-Qing Zhao

Beilstein J. Org. Chem. 2013, 9, 2852–2861, doi:10.3762/bjoc.9.321

• view angles [1][2]. More interestingly, DLCs can self-organize into columnar mesophases with a high degree of order, and show fast unidirectional charge migration properties, and have been studied as soft organic semiconductors [3][4][5][6][7][8][9][10][11][12]. Solution-processed and ink-jet printing

• (Colro) and hexagonal columnar mesophases (Colho). Furthermore, the structure-mesomorphic property relationship is discussed. The synthetic route is shown in Scheme 1 and Scheme 2. Results and Discussion Synthesis and characterization We synthesized the key intermediate 1, 2-hydroxy-3,6,7,10,11-pentakis

Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles

• Daniel J. Tate,
• Rémi Anémian,
• Richard J. Bushby,
• Suwat Nanan,
• Stuart L. Warriner and
• and Benjamin J. Whitaker

Beilstein J. Org. Chem. 2012, 8, 120–128, doi:10.3762/bjoc.8.14

• low-angle X-ray diffraction. The DSC data is summarised in Table 2, the phase behaviour of the isoalkyl series is compared graphically with that for the n-alkyl series in Figure 1 and typical polarizing micrographs are shown in Figure 2. Compounds 7b and 7c exhibit Colh columnar mesophases. For

Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases

• Eugen Wuckert,
• Constanze Hägele,
• Frank Giesselmann,
• Angelika Baro and
• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 57, doi:10.3762/bjoc.5.57

• not show any mesomorphic properties, whereas compounds 2e–i with C9–C13 chains displayed rectangular columnar mesophases and compounds 2j–l with C14–C16 chains displayed hexagonal columnar mesophases. Furthermore an anomalous odd-even effect of the clearing points of compounds 2e–l versus chain length

• was detected. Keywords: columnar mesophases; discotic liquid crystals; tetraphenylene; Introduction Columnar liquid crystals have received increasing interest during the last decade due to their 1D charge transport and self-healing properties, which make them particularly promising candidates for

• with peripheral alkoxy or alkanoate chains displayed smectic mesophases in addition to columnar phases, whereas the corresponding tetraphenylenes with p-alkoxybenzoate substituents displayed only columnar mesophases even with long chain lengths [29][30][31]. Thus, we anticipated that the presence of

Functional properties of metallomesogens modulated by molecular and supramolecular exotic arrangements

• Alessandra Crispini,
• Mauro Ghedini and
• Daniela Pucci

Beilstein J. Org. Chem. 2009, 5, No. 54, doi:10.3762/bjoc.5.54

• while the half-disc-shaped curcuminoids (B in Figure 2) self-assemble with the formation of columnar mesophases. Moreover, the presence of biologicaly active fragments (the O,O chelating ligands) induces promising anticancer activity in vitro against two human prostatic cancer cell lines in all these

Novel banana-discotic hybrid architectures

• Hari Krishna Bisoyi,
• H. T. Srinivasa and
• Sandeep Kumar

Beilstein J. Org. Chem. 2009, 5, No. 52, doi:10.3762/bjoc.5.52

• interesting physical properties important for device applications. If such architectures could provide columnar mesophases then the charge carrier mobilities are expected to increase owing to the presence of conducting aromatic bent-cores in the otherwise insulating alkyl chain mantle around the discotic

• the other hand, most of the discotic liquid crystalline compounds form columnar phases because of the strong π-π interaction of poly aromatic cores. In the columnar mesophases, the discotic molecules stack one on top of the other to form columns and the columns so formed arrange themselves in various

Synthesis of mesogenic phthalocyanine-C₆₀ donor–acceptor dyads designed for molecular heterojunction photovoltaic devices

• Yves Henri Geerts,
• Olivier Debever,
• Claire Amato and
• Sergey Sergeyev

Beilstein J. Org. Chem. 2009, 5, No. 49, doi:10.3762/bjoc.5.49

• thermal and photochemical stability [30]. Phthalocyanines bearing flexible peripheral substituents form columnar mesophases [8][31], which demonstrate very efficient charge transport along the columns [32][33]. A unique combination of properties makes phthalocyanines excellent candidates as active

• the previous finding that the pseudosymmetrical phthalocyanine 3 bearing four such substituents is very soluble in many organic solvents, forms columnar mesophases over a broad temperature range and, at the same time, possesses a reasonably low clearing point (ca. 180 °C) [46]. Finally, a critical