J-aggregates in matrix stabilized two-dimensional azobenzene derivatives

Shankar, Bhaskaran; Patnaik, Archita

doi:10.1016/j.jcis.2006.06.005

Cited by 10 publications

(5 citation statements)

References 46 publications

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“…The absorption maximum wavelength of the GlcAzo component of GlcC 18 -GlcAzo-tube dispersed in water at 25 °C ( λ max = 335 nm) was comparable with that of free GlcAzo dispersed in water after decomposition of the nanotube at 90 °C ( λ max = 334 nm), indicating that the GlcAzo component was individually embedded in the monolayer membrane wall. In contrast, the absorption maximum wavelength of the GlcGlyAzo component of GlcC 18 -GlcGlyAzo-tube dispersed in water at 25 °C ( λ max = 353 nm) was red-shifted compared with that of free GlcGlyAzo dispersed in water after decomposition of the nanotube at 90 °C ( λ max = 330 nm), indicating that the GlcGlyAzo component existed as a J -type aggregate 20 in the monolayer membrane wall.…”

Section: Resultsmentioning

confidence: 86%

Photo-responsive hole formation in the monolayer membrane wall of a supramolecular nanotube for quick recovery of encapsulated protein

Kameta

Kikkawa²,

Norikane³

2022

Nanoscale Adv.

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Section: Resultsmentioning

confidence: 86%

Photo-responsive hole formation in the monolayer membrane wall of a supramolecular nanotube for quick recovery of encapsulated protein

Kameta

Kikkawa²,

Norikane³

2022

Nanoscale Adv.

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“…Notably, the 319 nm peak is red-shifted by 21 nm compared to the π→π* transition of free trans - red - azo - PC monomers measured in CHCl 3 (Supporting Information, Figure S2). This bathochromic shift suggests the influence of solvatochromic effects − and potentially J-type coupling − due to the alignment of the chlorinated azobenzene groups in a bilayer configuration.…”

Section: Results and Discussionmentioning

confidence: 98%

Optical Membrane Control with Red Light Enabled by Red-Shifted Photolipids

et al. 2021

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Photoswitchable phospholipids, or “photolipids”, that harbor an azobenzene group in their lipid tails are versatile tools to manipulate and control lipid bilayer properties with light. So far, the limited ultraviolet-A/blue spectral range in which the photoisomerization of regular azobenzene operates has been a major obstacle for biophysical or photopharmaceutical applications. Here, we report on the synthesis of nano- and micrometer-sized liposomes from tetra-ortho-chloro azobenzene-substituted phosphatidylcholine (termed red -azo-PC) that undergoes photoisomerization on irradiation with tissue-penetrating red light (≥630 nm). Photoswitching strongly affects the fluidity and mechanical properties of lipid membranes, although small-angle X-ray scattering and dynamic light scattering measurements reveal only a minor influence on the overall bilayer thickness and area expansion. By controlling the photostationary state and the photoswitching efficiency of red -azo-PC for specific wavelengths, we demonstrate that shape transitions such as budding or pearling and the division of cell-sized vesicles can be achieved. These results emphasize the applicability of red -azo-PC as a nanophotonic tool in synthetic biology and for biomedical applications.

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“…[28][29][30] Among the molecular entities capable of forming ordered aggregates, azobenzenes are unique because of their intrinsic photoresponsive property. [31][32][33][34][35][36][37][38] Azobenzenes of donor-acceptor type have been found to form characteristic aggregates depending on the solvent composition, polarity, and the solute concentration.…”

Section: Introductionmentioning

confidence: 99%

Solvent‐Polarity‐Tunable Dimeric Association of a Fullerene (C₆₀)–N,N‐Dimethylaminoazobenzene Dyad: Modulated Electronic Coupling of the Azo Chromophore with a Substituted 3D Fullerene

Kumar

Patnaik

2011

Chemistry A European J

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The tunable self-assembly of a fullerene (C(60))-N,N-dimethylaminoazobenzene (DPNME) molecular system as a function of solvent polarity in THF/water binary solvent is reported. Gradual increase of the volume fraction of the nonsolvent water in a 1×10(-5) M THF solution of DPNME at a mixed dielectric constant ε(mix)≈42 resulted in initial redshifting of the (1)(π→π(*)) absorption band, which signified the 1D head-to-tail or J-type arrangement of the DPNME molecular system. Further increase in the solvent polarity to ε(mix)≈66 evidenced formation of an antiparallel head-to-tail or H-type molecular arrangement in conjunction with the J-aggregates, thereby establishing a solvent-polarity-dependent dynamic equilibrium between the monomer ↔ J-aggregate ↔ H-aggregate. The controlled aggregation was governed by the synergetic effect of intermolecular donor-acceptor interaction between the electron-deficient fullerene ring and the electron-rich N,N-dimethylamino-substituted aromatic ring; typically, van der Waals and π-π interactions between the molecules constituting a pair of dimers were envisaged. An agreement between the semiempirically calculated drastically reduced oscillator strength of the DPNME H-dimer in the antiparallel configuration (0.69 vs. 1.29 in the monomeric DPNME) and the experimental electronic absorption spectra beyond ε(mix)=66 further strengthened this assignment to the hitherto forbidden antiparallel H-dimer. Complementing the above, the periodicity of molecular self-assembly dictated a monoclinic unit cell in the single-crystal XRD packing pattern with a C2/c space group; the molecules packed laterally with mutual interdigitation with the donor (E)-N,N-dimethyl-4-(p-tolyldiazenyl)aniline (AZNME) parts in an antiparallel fashion (contrary to the usual expectation for H-aggregates) with strong inter- and intrapair van der Waals and π-π interactions between the constituent fullerene moieties. Unlike those of porphyrin/phthalocyanine bowl-like donor-initiated architectures, a rare class of DPNME dyadic supramolecular self-assemblies was realized with π-extended 2D fullerene networks, in which the linear geometry of the AZNME donor and the conformational rigidity of the fullerene acceptor played crucial roles.

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J-aggregates in matrix stabilized two-dimensional azobenzene derivatives

Cited by 10 publications

References 46 publications

Photo-responsive hole formation in the monolayer membrane wall of a supramolecular nanotube for quick recovery of encapsulated protein

Photo-responsive hole formation in the monolayer membrane wall of a supramolecular nanotube for quick recovery of encapsulated protein

Optical Membrane Control with Red Light Enabled by Red-Shifted Photolipids

Solvent‐Polarity‐Tunable Dimeric Association of a Fullerene (C₆₀)–N,N‐Dimethylaminoazobenzene Dyad: Modulated Electronic Coupling of the Azo Chromophore with a Substituted 3D Fullerene

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J-aggregates in matrix stabilized two-dimensional azobenzene derivatives

Cited by 10 publications

References 46 publications

Photo-responsive hole formation in the monolayer membrane wall of a supramolecular nanotube for quick recovery of encapsulated protein

Photo-responsive hole formation in the monolayer membrane wall of a supramolecular nanotube for quick recovery of encapsulated protein

Optical Membrane Control with Red Light Enabled by Red-Shifted Photolipids

Solvent‐Polarity‐Tunable Dimeric Association of a Fullerene (C60)–N,N‐Dimethylaminoazobenzene Dyad: Modulated Electronic Coupling of the Azo Chromophore with a Substituted 3D Fullerene

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Solvent‐Polarity‐Tunable Dimeric Association of a Fullerene (C₆₀)–N,N‐Dimethylaminoazobenzene Dyad: Modulated Electronic Coupling of the Azo Chromophore with a Substituted 3D Fullerene