Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization

• Wentao Yu,
• Zhiyao Yang,
• Chengkan Yu,
• Xiaowei Li and
• Lihua Yuan

Beilstein J. Org. Chem. 2025, 21, 179–188, doi:10.3762/bjoc.21.10

• ]. This is not only due to their rich host–guest chemistry but also due to π-surface-enabled self-assembly that enables the creation of various supramolecular structures, such as discotic liquid crystals [33], nanodimers [34], and organic frameworks [35]. Among them, shape-persistent hydrogen-bonded

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

• an effective tool for the design of liquid crystalline materials [3][4][5][6][7][8]. Rod-like liquid crystalline molecules with fluorine-substituted arenes are ubiquitous in the displays industry [12]. They are also gaining importance in the design of π-conjugated polycyclic aromatic discotic liquid

• reported the high versatility of these intermolecular interactions in the design of several Janus-like discotic mesogens (Figure 1) [44][45][46][47]. A first study dealt with the synthesis of two sets of compounds, namely 1,2,3,4-tetrafluoro-6,7,10,11-tetraalkxoytriphenylenes (4F-TPn) and 9,10,11,12,13,14

• derivatives: the in situ prepared 2Li-BP5/6 was reacted with F5/6 to yield the symmetrical discotic dimers, G55/G66 respectively, in an average yield of 42–45% (Scheme 1). The reaction of 2Li-BP8 with F4 was also successfully tested, and allowed the preparation of the unsymmetrical discotic dimer G48

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

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• Cheng [63] designed a click inspired synthesis of novel discotic mesogen bearing a porphyrin unit, a triazole linkage, and a peripheral 3,4,5-trialkoxybenzyl unit (Scheme 32). Firstly, free-base porphyrin conjugates 151a–c were obtained by the CuAAC reaction between metal free tetraalkynylporphyrin 149

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

• David Straßburger,
• Svenja Herziger,
• Katharina Huth,
• Moritz Urschbach,
• Rainer Haag and
• Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

• recently reported the successful application of functional supramolecular polymers in a biological context [30]. By decoration of the discotic peptide amphiphile monomers with dendritic mannose moieties, a specific cell targeting of macrophages and internalization in those antigen presenting cells has been

• structures modified with sulfate groups, and their capability to interact with biological components has been demonstrated recently [31][32]. In this work, we therefore coupled dPGS to C2-symmetrical discotic peptide amphiphiles using copper-catalyzed azide alkyne cycloaddition chemistry. The evaluation of

The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles

• Joscha Vollmeyer,
• Ute Baumeister and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 910–920, doi:10.3762/bjoc.10.89

• planar. Keywords: discotic liquid crystals; shape-persistent macrocycles; templates; X-ray scattering; Introduction The supramolecular chemistry of shape-persistent macrocycles has enormously expanded during the past several years [1][2][3][4][5][6]. It covers the non-covalent interaction between the

• naphthylene corners allow an efficient surrounding of the macrocycles with an alkyl fringe, according to the general design principle for discotic liquid crystals [47]. In addition to the macrocycles with intraannular bridges, we also synthesized and investigated a corresponding compound with an empty

• that the periphery of discotic molecules generally dominates their thermal behavior. Shortening the side chains usually increases the melting point, whereas longer side chains or branched alkyl groups have the opposite effect [47][52][53]. However, when the side groups become too long or bulky, the

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

• Bin Han Ping Hu Bi-Qin Wang Carl Redshaw Ke-Qing Zhao College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610066, China Department of Chemistry, University of Hull, Hull, HU6 7RX, UK 10.3762/bjoc.9.321 Abstract The synthesis of star-shaped discotic liquid crystal

• trimers using Co2(CO)8-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition reaction is reported. The trimers consist of three triphenylene discotic units linked to a central 1,2,4-trisubstituted benzene ring via flexible spacers. The trimers were synthesized in the yields up to 70% by mixing the monomers

• mesomorphism. Keywords: Co2(CO)8 catalyzed cycloaddition; columnar mesophase; discotic liquid crystal; triphenylene; oligomer; Introduction Discotic liquid crystals (DLCs) with nematic phase have been commercially utilized in the liquid crystal display industry as optical compensating films for widening the

Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies

• Jeelani Basha Shaik,
• Venkatachalam Ramkumar,
• Babu Varghese and
• Sethuraman Sankararaman

Beilstein J. Org. Chem. 2013, 9, 698–704, doi:10.3762/bjoc.9.79

• find application in the areas of molecular electronics, organic discotic liquid crystals and OLEDs [24][25]. One of the ways to approach the synthesis of these interesting compounds is to carry out multiple C–C coupling reactions with suitable polybromoarene derivatives. In multiple C–C coupling

Efficient electroorganic synthesis of 2,3,6,7,10,11-hexahydroxytriphenylene derivatives

• Carolin Regenbrecht and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2012, 8, 1721–1724, doi:10.3762/bjoc.8.196

• common structural motif. The use of triphenylenes in discotic liquid crystals [1][2] as building blocks in supramolecular chemistry [3][4] as well as in solid-state chemistry [5] is well documented. Furthermore, triphenylenes are applied as components of functional polymers [6][7] and fluorescent labels

Liquid-crystalline heterodimesogens and ABA-heterotrimesogens comprising a bent 3,5-diphenyl-1,2,4-oxadiazole central unit

• Govindaswamy Shanker,
• Marko Prehm and
• Carsten Tschierske

Beilstein J. Org. Chem. 2012, 8, 472–485, doi:10.3762/bjoc.8.54

• rod-like with discotic [1][9][10], phasmidic or bent-core units, linked together through flexible chains [1]. These flexible chains, which in most cases represent linear alkyl chains, connect the distinct mesogenic units, but depending on their length and degree of flexibility they can also decouple

Liquid-crystalline nanoparticles: Hybrid design and mesophase structures

• Gareth L. Nealon,
• Romain Greget,
• Cristina Dominguez,
• Zsuzsanna T. Nagy,
• Daniel Guillon,
• Jean-Louis Gallani and
• Bertrand Donnio

Beilstein J. Org. Chem. 2012, 8, 349–370, doi:10.3762/bjoc.8.39

• classified according to their general shape characteristics. Thus, rodlike or calamitic molecules, for example, possess one axis much longer than the others, whereas discotic molecules exhibit one axis much shorter than the other two (Figure 1). There are a variety of liquid-crystalline phases possible

• sample. Nanoparticles coated with discotic proto-mesogenic ligands Discotic mesogens are those which display one molecular axis considerably shorter than the other two, and they are extensively investigated [89][90] due to their potential use in a variety of high-technology applications [89], perhaps

• diameter coated with triphenylene based mesogenic thiols 236,6 (Figure 25) were prepared by using the direct method to give a surface exclusively coated with the discotic ligands [93]. These materials did not display mesomorphism in the neat state, but were readily dispersed into the columnar phase of

Synthesis of oleophilic electron-rich phenylhydrazines

• Aleksandra Jankowiak and
• Piotr Kaszyński

Beilstein J. Org. Chem. 2012, 8, 275–282, doi:10.3762/bjoc.8.29

• preparation of a discotic liquid crystal. Results and Discussion Our initial attempts at the preparation of 3,4-dioctyloxyphenylhydrazine (1a) focused on deprotection of the trichloroethyl ester 3a under buffered reductive conditions, according to the general literature procedure [24]. In aqueous MeOH

Laterally substituted symmetric and nonsymmetric salicylideneimine-based bent-core mesogens

• Sonja Findeisen-Tandel,
• Wolfgang Weissflog,
• Ute Baumeister,
• Gerhard Pelzl,
• H. N. Shreenivasa Murthy and
• Channabasaveshwar V. Yelamaggad

Beilstein J. Org. Chem. 2012, 8, 129–154, doi:10.3762/bjoc.8.15

• columnar (Col) phases were discovered in disklike (discotic) mesogens; such mesogens also exhibit nematic behaviour like that of calamitics. In fact, a survey of the literature shows clearly that molecules with a bent (banana) shape prepared earlier than discotics by Vorlaender (in 1929) possess the

• ]. Tris(salicylideneanilines) having a discotic shape exhibit a room-temperature columnar mesophase [18][19]. Dendromesogens containing up to 64 peripheral mesogenic salicylideneimine fragments have also been reported [20]. Antiferroelectric behaviour has been claimed by Yablonski et al. to be exhibited

Progress in liquid crystal chemistry II

• Sabine Laschat

Beilstein J. Org. Chem. 2012, 8, 118–119, doi:10.3762/bjoc.8.13

• , the chemistry behind liquid crystals, and particularly the synthesis, is the platform for such tremendous technological achievements, and this is true for both calamitic (rod-like) as well as discotic (disk-shaped) or other types of liquid crystals [2][3][4]. Since our initial Thematic Series

• W. Goodby to find more detailed information [6]. The review articles and original research papers of this second Thematic Series in the Beilstein Journal of Organic Chemistry, written by known experts of their field, cover diverse topics such as novel discotic and calamitic compounds, bent-core

Self-assembled ordered structures in thin films of HAT5 discotic liquid crystal

• Piero Morales,
• Jan Lagerwall,
• Paolo Vacca,
• Sabine Laschat and
• Giusy Scalia

Beilstein J. Org. Chem. 2010, 6, No. 51, doi:10.3762/bjoc.6.51

• . R. Portici, P.le E. Fermi, I-80055 Portici (Naples) Italy Institute of Organic Chemistry, University of Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany 10.3762/bjoc.6.51 Abstract Thin films of the discotic liquid crystal hexapentyloxytriphenylene (HAT5), prepared from solution via casting

• compared to the bulk situation, where the same material crystallizes into a polymorphic structure at 68 °C. Keywords: AFM; discotic liquid crystals; hexapentyloxytriphenylene; self-organization; thin films; Introduction Discotic liquid crystals are an interesting type of organic semiconductors that allow

• for discotic LCs. Without a macroscopic, uniform alignment the excellent properties of discotic LCs cannot be expressed at their best. Moreover, the ability to select the direction of the column alignment is also desirable since the optimum direction depends on the application [7]. Use of discotics as

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

• 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

• ][30]. Furthermore, anomalous odd-even effects were discovered for these discotic tetraphenylenes, i.e. the ascending and descending transition temperatures with increasing numbers of methylene groups in the side chain exhibit an inversion of this alternation between n = 12 and n = 14 homologues [31

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

• the ancillary ligand. Indeed a transition from a calamitic to a columnar mesophase is observed, through a calamitic/discotic cross-over point, due to the peculiar combination of two different molecular architectures. The mononuclear tropolonate derivative (A in Figure 2) shows a chiral nematic phase

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

• Hari Krishna Bisoyi H. T. Srinivasa Sandeep Kumar Raman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore, India. Phone: +91 80 23610122, Fax: +91 80 23610492 10.3762/bjoc.5.52 Abstract Here we present the design and synthesis of novel banana-discotic dimers and banana-bridged

• discotic dimers. The chemical structures have been characterized by spectral techniques and elemental analysis. The thermal behaviors of the compounds have been investigated by polarizing optical microscopy and differential scanning calorimetry. None of these synthesized compounds exhibit any liquid

• crystalline property probably because of the incompatibility of the bent-core with the discotic core. Keywords: bent-core; dimer; discotic; triphenylene; Introduction Liquid crystals are unique functional self-organized soft materials which possess order and dynamics. Recently, banana liquid crystals or

Progress in liquid crystal chemistry

• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 48, doi:10.3762/bjoc.5.48

• diverse topics such as phthalocyanine-fullerene hybrid materials for photovoltaic devices, functional metallomesogens, coaxial electrospinning of liquid crystal-containing microfibers, banana-discotic hybrid systems, ionic liquid crystals, relations between molecular length distribution and formation of

• smectic phases, nematic phase engineering by using V-shaped molecules, saddle-shaped columnar systems displaying anomalous odd-even effects, theoretical studies on the origin of chirality transfer in liquid crystalline host-guest systems, liquid crystalline carboranes and dyes and discotic phenanthrene

Shape- persistent macrocycle with intraannular alkyl groups: some structural limits of discotic liquid crystals with an inverted structure

• Sigurd Höger,
• Jill Weber,
• Andreas Leppert and
• Volker Enkelmann

Beilstein J. Org. Chem. 2008, 4, No. 1, doi:10.1186/1860-5397-4-1

• defined surfaces [1][2][3][4][5][6][7][8]. Furthermore, shape-persistent macrocycles are interesting mesogens for discotic liquid crystalline materials [9][10][11][12]. The common design principle of conventional discotic liquid crystals (LCs) is a more or less rigid core (disk-like or macrocyclic) with

• of the compound. The term adaptable means that the orientation of substituents at that position can be influenced by an external parameter [25][26]. Compound 1 melts at 134 °C to form a nematic mesophase that becomes isotropic at 159 °C. However, compared to all previously reported discotic LCs, this

• compound is composed of a rigid periphery and the flexible side chains point inward. Hence, 1 can be described as a discotic LC with an inverted structure (Figure 1) [23][24]. By comparing the structure of 1, and other shape-persistent macrocycles, with their thermal behavior we could identify some