A Synthetic Amino Acid Residue Containing A New Oligopeptide‐Based Photosensitive Fluorescent Organogel

Maiti, Dibakar Kumar; Banerjee, Arindam

doi:10.1002/asia.201200617

Cited by 51 publications

(32 citation statements)

References 149 publications

(44 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Oligo(ethylene glycol) substituted styrene derivatives, 13 bis(4-acetoxyphenyl) disulphide 14 and 4-acetoxystyrene 15 were prepared according to the literature procedures. 4-Vinylbenzoic acid was purchased from Sigma-Aldrich Japan.…”

Section: Methodsmentioning

confidence: 99%

Facile modification and fixation of diaryl disulphide-containing dynamic covalent polyesters by iodine-catalysed insertion-like addition reactions of styrene derivatives to disulphide units

et al. 2016

View full text Add to dashboard Cite

We report the modification of diaryl disulphide-containing dynamic covalent polyesters (DADS-PEs) via an iodine-catalysed addition reaction with styrene derivatives that proceeds in an insertion-like manner. The simple procedure of these reactions enabled facile control of the primary structure and physical properties of DADS-PEs by using various styrene derivatives with several polar substituents, flexible oligomeric chains, and two vinyl functionalities that work as a cross-linker. The addition reactions were also found to be an efficient method for "fixing" the polymer structure via conversion of dynamic diaryl disulphide bonds, which are susceptible to bond exchange reactions under photo-irradiation. † Electronic supplementary information (ESI) available: GPC curves, 1 H NMR spectra and the photographs of the film samples. See

show abstract

Section: Methodsmentioning

confidence: 99%

Facile modification and fixation of diaryl disulphide-containing dynamic covalent polyesters by iodine-catalysed insertion-like addition reactions of styrene derivatives to disulphide units

et al. 2016

View full text Add to dashboard Cite

show abstract

“…[10] Among the stimuli-responsive organogels, photo-responsive organogels have attracted considerable attention because light is a non-contaminating stimulus that provides a broad range of tunable parameters. And the photo-responsive organogels possess ample applications in light harvesting, [11] fluorescent scensing, [12,13] light switching, [14] etc. Photo-responsive azobenzene moieties have been widely used in supramolecular chemistry by virtue of the large photoinduced changes in their molecular geometries and physical properties due to the trans-cis isomerization of N＝N bond, and a large number of gelators comprising azobenzene units have been reported.…”

Section: Introductionmentioning

confidence: 99%

A Photo‐Responsive Organogel Based on Pyrene‐Substituted Acylhydrazone Derivative

et al. 2017

View full text Add to dashboard Cite

A new simple pyrene‐substituted acylhydrazone derivative, 4‐(3,4‐dioctyloxy) phenyl‐1‐pyrene acylhydrazone (PAH‐8), was designed and synthesized. The PAH‐8 can form thermo‐reversible organogel in DMSO, and shows gelation‐induced enhanced fluorescence emission. Xerogel exhibits ribbon‐like fibrous aggregates with widths of 0.5‐1 μm. The PAH‐8 organogel indicates photo‐responsive behaviors due to the trans‐cis isomerizations of ‐C=N‐ bond upon exposure to visible or UV light. Upon visible light irradiation, the partial trans‐cis isomerization of the ‐C=N‐ bond causes the fiber morphology to disappear, resulting in gel‐sol transition, whereas the PAH‐8 organogel exhibits few photoisomerizations from trans to cis transition without breakage of the gel state upon UV light irradiation.

show abstract

“…Supramolecular soft materials [1][2][3][4][5][6][7][8][9][10] have become a rapidly expanding area in current research for the last few years. Among these soft materials, low molecular weight hydrogelators (LMWHG) [11][12][13][14][15][16] are currently finding potential applications in drug delivery, tissue engineering, bio-sensing and other related fields.…”

Section: Introductionmentioning

confidence: 99%

Two-Component Fluorescent-Semiconducting Hydrogel from Naphthalene Diimide-Appended Peptide with Long-Chain Amines: Variation in Thermal and Mechanical Strengths of Gels

et al. 2016

Self Cite

View full text Add to dashboard Cite

Two-component fluorescent hydrogels have been discovered, containing the mixtures of naphthalene diimide (NDI)-conjugated peptide-functionalized bola-amphiphile and primary amines with long alkyl chains at physiological pH 7.46. The aggregation-induced enhanced emission associated with an NDI-appended peptide in aqueous medium is rare, as water is known to be a good quencher of fluorescence. In this study, an NDI-containing gelator peptide forms a highly fluorescent aggregate in aqueous medium. Absorption and emission spectroscopic techniques reveal the formation of J-aggregates among the chromophoric moieties in their aggregated state in aqueous medium. However, this NDI-containing peptide does not form any gel in aqueous medium. In the presence of the primary amines with long alkyl chains in the buffer solution, it forms two-component fluorescent hydrogels exhibiting bright yellow fluorescence under a UV lamp (365 nm). Probably, the acid-amine interaction between the amines and the bola-amphiphile triggers the gel formation, as evident from Fourier transform infrared data, indicating the presence of a carboxylate group (-COO) and an ammonium species (NH) in the coassembled two-component gel system. Low- and wide-angle powder X-ray diffraction and small-angle X-ray scattering further support the fact that the coassembled state in the gel form is produced by the supramolecular interaction between the NDI-based bola-amphiphile and the long-chain amines. Field-emission scanning electron microscopy and high-resolution transmission electron microscopy images reveal that the π-conjugated coassembled hydrogels exhibit nanofibrillar network morphologies. Interestingly, the coassembled hydrogels exhibit an enhanced fluorescence emission, excited-state lifetime, and quantum yield when compared with those of the NDI-containing amphiphile alone in its self-assembled state in aqueous medium. Moreover, the thermal stability and mechanical strength of these gels have been successfully tuned by varying the alkyl chain length of the corresponding amine. Moreover, these NDI-peptide-conjugated soft materials exhibit semiconducting behavior in their respective coassembled states. This holds future promise to use these peptide-appended NDI-based coassembled soft materials for applications in optoelectronic and other devices.

show abstract

A Synthetic Amino Acid Residue Containing A New Oligopeptide‐Based Photosensitive Fluorescent Organogel

Cited by 51 publications

References 149 publications

Facile modification and fixation of diaryl disulphide-containing dynamic covalent polyesters by iodine-catalysed insertion-like addition reactions of styrene derivatives to disulphide units

Facile modification and fixation of diaryl disulphide-containing dynamic covalent polyesters by iodine-catalysed insertion-like addition reactions of styrene derivatives to disulphide units

A Photo‐Responsive Organogel Based on Pyrene‐Substituted Acylhydrazone Derivative

Two-Component Fluorescent-Semiconducting Hydrogel from Naphthalene Diimide-Appended Peptide with Long-Chain Amines: Variation in Thermal and Mechanical Strengths of Gels

Contact Info

Product

Resources

About