- Novel fluorescent perylene liquid crystal with diphenylacrylonitrile groups: Observation of a large pseudo stokes shift based on AIE and FRET effects
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A novel perylene liquid crystal with diphenylacrylonitrile groups on 1,7-bay positions was synthesized in high yield. This highly decorated perylene bisimide showed the ordered hexagonal columnar liquid crystalline behaviour between 124.9 and 189.5 °C. Up
- Zhu, Mingguang,Zhuo, Youzhen,Cai, Kaicong,Guo, Hongyu,Yang, Fafu
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- Tweaking a BODIPY Spherical Self-Assembly to 2D Supramolecular Polymers Facilitates Excited-State Cascade Energy Transfer
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Excited state properties such as emission, exciton transport, electron transfer, etc., are strongly dependent on the shape, size and molecular arrangement of chromophore based supramolecular architectures. Herein, we demonstrate creation and control of distinct supramolecular energy landscapes for the reversible control of the excited-state emission processes through cascade energy transfer in chromophore assemblies, facilitated by an unprecedented solvent effect. In methylcyclohexane, a tailor-made Y-shaped BODIPY derivative self-assembles to form an unusual spherical architecture of 400–1200 nm size, which exhibits a single emission at 540 nm upon 475 nm excitation through a normal excitation deactivation process. However, in n-decane, the same BODIPY derivative forms two-dimensional supramolecular sheets, exhibiting multiple emission peaks at 540, 610, 650, 725 and 790 nm with 475 nm excitation due to cascade energy transfer. Further control on the morphology and excitation energy transfer is possible with variable solvent composition and ultrasound stimulation, resulting in enhanced near-infrared emission with an overall pseudo Stokes shift of 7105 cm?1.
- Das, Gourab,Cherumukkil, Sandeep,Padmakumar, Akhil,Banakar, Vijay B.,Praveen, Vakayil K.,Ajayaghosh, Ayyappanpillai
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p. 7851 - 7859
(2021/03/08)
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- Novel perylene columnar liquid crystal tuned by azo isomerization on bay-positions
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Two azo-perylene derivatives (PBI-AZO-1 and PBI-AZO-2) with two alkyl chains and six alkoxy chains were designed and synthesized in yield of 63% and 49%, respectively. PBI-AZO-1 showed no mesophase but PBI-AZO-2 exhibited ordered hexagonal columnar mesophase based on the favorable effects of multiple alkyl chains. PBI-AZO-1 and PBI-AZO-2 exhibited the cis and trans azo-isomerization under radiation of UV light and the fluorescence quantum yields enhanced remarkably from 0.61 and 0.64 to 0.78 and 0.88, respectively. The ordered hexagonal columnar mesophase of PBI-AZO-2 was destroyed by isomerization due to the influence of asymmetrical mixture of cis and trans isomers. The transformation of liquid crystal/non-liquid crystal of PBI-AZO-2 before and after cis/trans isomerization displayed good reversibility by storing the sample for 15 days at room temperature. This kind of liquid crystallic behavior tuned by azo isomerization was first observed for perylene liquid crystal.
- Lin, Jianrong,Ji, Xiaoyu,Guo, Hongyu,Yang, Fafu
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- Preparation method and application for amphiphilic naphthoyl diimide gelator
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The invention belongs to the technical field of supramolecular chemistry, and specifically relates to a preparation method and an application for an amphiphilic naphthoyl diimide gelator. The amphiphilic naphthoyl diimide gelator provided by the invention has a molecular formula of C89H138N4O21, and can enable benzene, toluene, xylene, dimethyl sulfoxide (DMSO) or a tetrahydrofuran solution with awater content of 30% (H2O-THF with a concentration of 30%) to generate gelation at a low concentration (3.3 mg.mL to 9.5 mg.mL through a heating-cooling method. Meanwhile, the molecular gel formed by gelation can realize reversible conversion between a solution state and a gel state through the external action of heating-cooling. The gelator provided by the invention has the advantages ofsimple synthesis, easily modified structure, thermal reversibility, large polarity range of a gelated solvent, etc., and has potential application values in fields like catalysis, sensor technologies, drug delivery and chiral separation.
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Paragraph 0031; 0034; 0036; 0038
(2018/04/02)
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- Preparation method and application of naphthalene diimide gelator with symmetric structure
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The invention discloses a preparation method and application of a naphthalene diimide gelator with a symmetric structure. The naphthalene diimide gelator with the symmetric structure has a molecular formula: C104H168N4O12 and is capable of gelatinizing cyclohexane, benzene, methylbenzene and dimethylbenzene under low concentration (4.0mg mL-9.8mg mL) by using a heating-cooling method. In addition, molecular gel formed after gelatinization is reversible between a solution state and a gel state under an external action of heating-cooling or mechanical oscillation. The gelator provided bythe invention is simple in synthesis and easily-modified in structure, has the advantages such as thermal reversibility, oscillation stimulation responsiveness and the like and has a potential application value in the field such as catalysis, sensing technologies, drug delivery and chiral separation.
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Paragraph 0030; 0033; 0037
(2018/10/02)
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- Perylene liquid crystals with multiple alkyl chains: Investigation of the influence of peripheral alkyl chain number on mesomorphic and photophysical properties
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Herein, a series of mesogenic perylene bisimide (PBI) dyes including 1,6,7,12-tetrachloroperylenebisimides 11a, 11b and 11c with 2, 4 and 6 peripheral alkyl chains at the imide positions and 1,6,7,12-tetra-p-nonylphenol bay-substituted perylene bisimides 12a, 12b and 12c with 6, 8 and 10 peripheral alkyl chains at both the imide and bay-positions were synthesized and characterized. The influence of multiple peripheral alkyl chains on the mesomorphic and photophysical properties was investigated. The results suggested that all of them possessed hexagonal columnar mesophases. The presence of more alkyl chains contributed to lower phase transition temperature and more orderly hexagonal mesophases. These novel perylene liquid crystals exhibited excellent fluorescence properties with fluorescence quantum yields of 0.90-0.96 in solution. The compounds 12a, 12b and 12c presented larger Stoke shifts and higher ΦF values than the compounds 11a, 11b and 11c; this indicated that more peripheral alkyl chains at both the imide and bay-positions contributed to the excellent fluorescence properties in both solution and thin films.
- Zhu, Mingguang,Chen, Yongzhu,Guo, Hongyu,Yang, Fafu,Song, Xuchun
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p. 8998 - 9005
(2018/06/08)
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- Seeded Supramolecular Polymerization in a Three-Domain Self-Assembly of an N-Annulated Perylenetetracarboxamide
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The three-domain cooperative supramolecular polymerization of 1, together with the lag time in which the monomeric species remains inactive, allows seeded supramolecular polymerization to be performed. The kinetic experiments demonstrate that only seeds based on the intermediate aggregate are able to propagate the supramolecular polymerization of 1 from their active sites. The results presented herein constitute a new example of kinetically controlled supramolecular systems and contribute to expanding knowledge about the structural requirements of a self-assembling molecule to experience seeded supramolecular polymerization.
- Greciano, Elisa E.,Sánchez, Luis
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p. 13724 - 13730
(2016/09/13)
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- Novel perylene liquid crystals: Investigation of the influence of bay-substituents on mesomorphism and photophysical property
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A series of perylene liquid crystals with H, Br, phenyl and tert-butylphenyl on bay-positions were synthesized in yields of 50-70%. Their mesomorphic properties and photophysical properties were investigated. The perylene derivatives 6, 7 and 8 with Br, phenyl and tert-butylphenyl at bay-positions have the hexagonal columnar liquid crystalline phase and wider scopes of phase transfer temperatures in comparison with similar perylene liquid crystal 5 with no substituent on bay-position. Compounds 6, 7 and 8 showed stronger fluorescence intensities, larger Stokes shifts and higher quantum yields than that of compound 5. These results indicated that the suitable substituents on bay-positions of perylene liquid crystals were favorable for producing excellent mesomorphic properties and good fluorescence properties.
- Zhu, Mingguang,Guo, Hongyu,Yang, Fafu,Wang, Zusheng
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p. 387 - 394
(2016/07/06)
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- Novel room-temperature thermotropic liquid crystals: Synthesis and mesomorphism of gallic-perylene-gallic trimers
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Three novel gallic-perylene-gallic trimers 7, 8 and 9 were synthesized by reacting gallic amino derivatives 3, 4 or 6 with perylene tetracarboxylic anhydride in yields of 75%, 78% and 80%, respectively. Compounds 7 and 8 with soft bridging chains exhibit
- Meng, Li,Wu, Qiumei,Yang, Fafu,Guo, Hongyu
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- Synthesis and mesomorphic properties of novel columnar liquid crystals based on polytopic gallic ethers with multiple-hydrogen bonding cyanuric cores
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The gallic-cyanuric monomer 4, gallic-cyanuric dimer 5, gallic-cyanuric trimer 6 and gallic-cyanuric tetramer 7 containing multiple hydrogen bond were designed and synthesized in yields of 70-80%. Their symmetric structures were characterized by element a
- Guo, Hongyu,Fang, Xiaoting,Yang, Fafu,Wu, Yamin
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p. 5465 - 5469
(2015/09/15)
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- Novel gallic-calixarene liquid crystals: Syntheses and conformation influences on mesomorphism
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Three novel gallic-calixarene derivatives 5, 6 and 7 were prepared in yields of 57-76%. Their structures and conformations were confirmed by element analyses, IR, ESI-MS and NMR spectra. Compounds 5 and 6 with stable cone conformation show liquid crystall
- Fang, Xiaoting,Guo, Hongyu,Yang, Fafu,Wu, Yamin
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p. 6128 - 6131
(2015/10/28)
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- Ultrasound stimulated nucleation and growth of a dye assembly into extended gel nanostructures
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A squaraine dye functionalized with a bulky trialkoxy phenyl moiety through a flexible diamide linkage (GA-SQ) capable of undergoing self-assembly has been synthesized and fully characterized. Rapid cooling of a hot solution of GA-SQ to 0 °C results in se
- Malicka, Joanna M.,Sandeep, Anjamkudy,Monti, Filippo,Bandini, Elisa,Gazzano, Massimo,Ranjith, Choorikkat,Praveen, Vakayil K.,Ajayaghosh, Ayyappanpillai,Armaroli, Nicola
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p. 12991 - 13001
(2013/10/01)
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- Cooperative self-assembly of linear organogelators. Amplification of chirality and crystal growth of pharmaceutical ingredients
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Linear organogelators 1 and 2, which self-assemble cooperatively into fibrillar structures, act as efficient crystal growth media for common pharmaceutical ingredients like ASP, CAF, IND and CBZ. This journal is
- Aparicio, Fatima,Matesanz, Emilio,Sanchez, Luis
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supporting information; experimental part
p. 5757 - 5759
(2012/07/14)
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- Self-assembly and conductivity of hydrogen-bonded oligothiophene nanofiber networks
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Symmetric oligothiophene derivatives containing hydrogen bond forming segments create self-supporting organogels consisting of self-assembled 1D nanostructures at low concentrations. Hydrogen bond formation and π-π stacking were both found to be crucial f
- Stone, David A.,Tayi, Alok S.,Goldberger, Joshua E.,Palmer, Liam C.,Stupp, Samuel I.
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p. 5702 - 5704
(2011/06/27)
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- An organogel system can control the stereochemical course of anthracene photodimerization
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A novel photoresponsive organogel with a binary gelator containing 2-anthracenecarboxylic acid shows a high degree of stereochemical control, resulting in head-to-head photocyclodimers exclusively together with significant enantiomeric excess induced by t
- Dawn, Arnab,Fujita, Norifumi,Haraguchi, Shuichi,Sada, Kazuki,Shinkai, Seiji
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supporting information; experimental part
p. 2100 - 2102
(2009/09/05)
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- Control of H- and J-type π stacking by peripheral alkyl chains and self-sorting phenomena in perylene bisimide homo- and heteroaggregates
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The synthesis, self-assembly, and gelation ability of a series of organogelators based on perylene bisimide (PBI) dyes containing amide groups at imide positions are reported. The synergetic effect of intermolecular hydrogen bonding among the amide functi
- Ghosh, Suhrit,Li, Xue-Qing,Stepanenko, Vladimir,Wuerthner, Frank
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scheme or table
p. 11343 - 11357
(2009/10/25)
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- Highly fluorescent lyotropic mesophases and organogels based on J-aggregates of core-twisted perylene bisimide dyes
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A new perylene bisimide dye based organogelator PBI1 with a sharp J-type absorption band and favorable emission properties was introduced. Gelation tests performed for PBI1 in 17 different organic solvents show no occurrence of gelation in solvents such a
- Li, Xue-Qing,Zhang, Xin,Ghosh, Suhrit,Wuerthner, Frank
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supporting information; experimental part
p. 8074 - 8078
(2009/10/10)
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- Organogels of 8-quinolinol/metal(II)-chelate derivatives that show electron- and light-emitting properties
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8-Quinolinol/copper(II)-, palladium(II)-, and platinum(II)-chelate-based organogelators (IM) and their nongelling reference compounds (2M) were synthesized. Complexes IM could gelate various organic solvents at very low concentrations. Electron microscope
- Shirakawa, Michihiro,Fujita, Norifumi,Tani, Takahiro,Kaneko, Kenji,Ojima, Masayoshi,Fujii, Akihiko,Ozaki, Masanori,Shinkai, Seiji
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p. 4155 - 4162
(2008/02/08)
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- Organogel of an 8-quinolinol platinum(II) chelate derivative and its efficient phosphorescence emission effected by inhibition of dioxygen quenching
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A newly synthesized 8-quinolinol platinum(II) chelate derivative gelates various organic solvents, and the gel formed shows unique thermo- and solvatochromism of visible and phosphorescent colour in response to a sol-gel phase transition and possesses an
- Shirakawa, Michihiro,Fujita, Norifumi,Tani, Takahiro,Kaneko, Kenji,Shinkai, Seiji
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p. 4149 - 4151
(2007/10/03)
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- Creation of a mixed-valence state from one-dimensionally aligned TTF utilizing the self-assembling nature of a low molecular-weight gel
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One-dimensional TTF assemblies have been obtained through the design of low molecular-weight gels, which show a characteristic absorption band at around 1750 nm upon I2 doping, assignable to a mixed-valence state of the TTF assemblies. Copyrigh
- Kitahara, Tatsuya,Shirakawa, Michihiro,Kawano, Shin-Ichiro,Beginn, Uwe,Fujita, Norifumi,Shinkai, Seiji
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p. 14980 - 14981
(2007/10/03)
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