Design, Synthesis, and Characterization of 1,3,5-Tri(1<i>H</i>-benzo[<i>d</i>]imidazol-2-yl)benzene-Based Fluorescent Supramolecular Columnar Liquid Crystals with a Broad Mesomorphic Range

Xiong, Jun; Luo, Sukun; Huo, Jingpei; Liu, Jinyan; Chen, Shuixia; Wang, Zhaoyang

doi:10.1021/jo5016954

Cited by 47 publications

(30 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Herein, we describe the key role of 1,3,5‐tri(1H‐benzo[ d ]imidazol‐2‐yl)benzene (TBIB) in the formation of programmable two‐ and three‐component ordered coassemblies driven by hydrogen bonding interaction. TBIB comprising three imidazole fragments with six alternative hydrogen bonding donor/acceptor sites behaves as a favorable binder to accommodate aromatic amino acid building units . The complexes of aromatic (Fmoc) amino acids and TBIB would undergo the self‐organization in aqueous media to form M ‐handed helical nanofibers ( Figure a–c), where the chirality transfers from amino acids to TBIB.…”

Section: Summary Of Assembly Parameters Based On Aromatic Amino Acid/mentioning

confidence: 99%

Programmable Multicomponent Self‐Assembly Based on Aromatic Amino Acids

et al. 2018

View full text Add to dashboard Cite

promising application potential especially in optoelectronics such as light-harvesting systems, organic light emitting diodes, and organic solar cells. [2] Construction of multicomponent assembly systems, in general, could be accomplished through several protocols. To fabricate two-component assemblies, one needs to overcome competitive selfsorting [3,4] of individual self-assemblies to achieve the coassembly. To this end, either strong binding interaction or considerable structural similarity between different components is a prerequisite. For instance, utilizing complementary hydrogen bonding and structural similarity, we have developed amino acid derivative-bipyridine coassembly systems for superchirality control, [5,6] and glutamic analogue coassembly for light harvesting. [7,8] Although some two-component assemblies could be predesigned, the realization of ordered coassembly comprising of three or more components is greatly restricted. [2,9,10] Exponentially increased complexity in three or four-component systems hinders ordered complexation and aggregation. Efforts that have been made in recent years regarding multicomponent systems are concentrated largely on the metallosupramolecular coordination chemistry [11] and dynamic covalent chemistry. [12] Transition metal ions could coordinate with different ligands [13] to form multicomponent metal organic frameworks (MOFs), [14] cages, [11] and molecular polyhedras. [15] Alternatively, orthogonal dynamic covalent bonds like BO and CN that feature easy formation upon dehydration have been employed to prepare metal-free molecular cages [16] and covalent organic frameworks (COFs). [17] Nevertheless, these methods, which place major emphasis on the crystallization process, could hardly be applied to fabricate soft molecular self-assemblies. [18] Utilization of orthogonal noncovalent interactions is a promising method to integrate independent species into coassemblies, with which numerous two or three-component supramolecular polymers have been built. [19] Most of these supramolecular polymeric systems still rely on metal-ligand coordination (such as terpyridine/Fe(III)) [20] and macrocyclic complexation (such as cucurbituril[8]) [21] between components. In many cases, intertwining polymer chains would result in chaotic molecular stacking rather than periodic and ordered molecular organization.Consequently, it is highly challenging to accomplish ordered molecular self-assembly, especially from three or more organic Construction of integrated self-assembly with ordered structures from two or more organic building blocks is currently a challenge, since it suffers from intrinsic systematic complexity and diverse competitive pathways. Here, it is reported that aromatic amino acid building units can be incorporated into two-or three-component coassembly driven primarily by hydrogen bonding interactions without the assistance of metal-ligand and macrocycle-based host-guest interactions. The key strategy is to employ a C 3 -symmetric molecule with alternative hydrogen ...

show abstract

Section: Summary Of Assembly Parameters Based On Aromatic Amino Acid/mentioning

confidence: 99%

Programmable Multicomponent Self‐Assembly Based on Aromatic Amino Acids

et al. 2018

View full text Add to dashboard Cite

show abstract

“…After polymerization of the acida nd removal of the template, ultimately, an anoporous membrane may be obtained. Following this design principle, we selected 1,3,5-tris(1 H-benzo[d]imidazol-2yl)benzene( TBIB), ac ompound knownt og ive LC mixtures with gallic acidd erivatives, [7] as the rigid core, and decided to investigate the formation of columnar DLC phases with fatty acids. Fatty acids have previously been used to form nematic and smectic LCs.…”

Section: Introductionmentioning

confidence: 99%

Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes

Lugger

2016

ChemistryOpen

View full text Add to dashboard Cite

We report the formation of easily accessible hydrogen‐bonded columnar discotic liquid crystals (LCs) based on tris‐benzoimidazolyl benzene (TBIB) and commercially available fatty acids. By increasing the length of the fatty acid, the temperature range of liquid crystallinity was tuned. Introducing double bonds in octadecanoic acid lowered the crystallization temperature and increased the temperature range of the mesophase. Surprisingly, dimerized linoleic acid also forms an LC phase. When using branched aliphatic acids with the branching point close to the acid moiety, the mesophase was lost, whereas phosphonic acid or benzenesulfonic acid derivatives did have a mesophase, showing that the generality of this approach extends beyond carboxylic acids as the hydrogen‐bond donor. Furthermore, a polymerizable LC phase was obtained from mixtures of TBIB with a methacrylate‐bearing fatty acid, providing an approach for the fabrication of nanoporous polymer films if the methacrylate groups are polymerized. Finally, the higher solubility of methyl‐TBIB was used to suppress phase separation in stoichiometric mixtures of the template molecule with fatty acids.

show abstract

“…[1][2][3][4] Especially, more and more importance has been attached to the benzimidazole drugs for their significant biological activities, e.g. anticancer, antifungal, antiviral, anti-inflammatory, etc.…”

Section: Introductionmentioning

confidence: 99%

“…[28][29][30][31][32][33][34][35][36][37] However, there is no report about the drug delivery of benzimidazole drugs loaded by PLA materials. Herein, on the basis of our previous studies on lactic acid (LA) direct melt polymerization [35,38,39] and benzimidazole compounds, [3][4][5][6] using AMB [10] as a model of benzimidazole-type drugs, poly(lactic acid-coaminomethyl benzimidazole) (PLAAMB) as a potential biodegradable drug-loaded polymer is designed, and synthesized (Scheme 1). After the discussions on the optimal synthetic conditions, the structures and basic properties of PLAAMBs with different molar feed ratios are systematically investigated by Fourier transform infrared (FT-IR), 1 H NMR, gel permeation chromatography (GPC), differential scanning calorimetry (DSC), and X-ray diffraction (XRD).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a novel drug-loaded polymer, poly(lactic acid-co-aminomethyl benzimidazole)

Hao

et al. 2015

Designed Monomers and Polymers

Self Cite

View full text Add to dashboard Cite

2015): Synthesis and characterization of a novel drug-loaded polymer, poly(lactic acid-co-aminomethyl benzimidazole), Designed Monomers and Polymers, Using aminomethyl benzimidazole (AMB) as a model of benzimidazole-type drugs, a potential biodegradable drug-loaded polymer poly(lactic acid-co-aminomethyl benzimidazole) (PLAAMB) is synthesized as designed via direct melt polycondensation starting from D,L-lactic acid (LA). When the molar feed ratio LA/AMB is 40/1, the optimal synthetic conditions, including catalyst type and dosage, polycondensation temperature, and copolymerization time are discussed. After the prepolymerization at 140°C for 8 h, using 0.4 wt% stannous oxide (SnO) as the catalyst, the melt copolymerization at 160°C for 6 h gives the copolymer with the biggest weight-average molecular weight (M w ) 5300 Da. The structure and properties of the copolymer are systematically characterized with Fourier transform infrared, 1 H NMR, gel permeation chromatography, differential scanning calorimetry, and X-ray diffraction. And the investigations on the influences of different molar feed ratios on the properties of PLAAMB show that, the copolymer PLAAMB with the biggest M w of 9400 Da can be obtained. After the drug model AMB as a monomer is introduced into polylactic acid during the condensation, the T g of the obtained PLAAMB is lower than the T g of homopolymer poly(D,L-lactic acid) (PDLLA). The M w and crystallinity of PLAAMBs can meet the requirement of drug-loaded polymers in the drug delivery.

show abstract

Design, Synthesis, and Characterization of 1,3,5-Tri(1H-benzo[d]imidazol-2-yl)benzene-Based Fluorescent Supramolecular Columnar Liquid Crystals with a Broad Mesomorphic Range

Cited by 47 publications

References 37 publications

Programmable Multicomponent Self‐Assembly Based on Aromatic Amino Acids

Programmable Multicomponent Self‐Assembly Based on Aromatic Amino Acids

Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes

Synthesis and characterization of a novel drug-loaded polymer, poly(lactic acid-co-aminomethyl benzimidazole)

Contact Info

Product

Resources

About