Dataset Information

Locked-Azobenzene: Testing the Scope of a Unique Photoswitchable Scaffold for Cell Physiology.

ABSTRACT: Azobenzenes are the most widely studied photoswitches, and have become popular optical probes for biological systems. The cis configuration is normally metastable, meaning the trans configuration is always thermodynamically favored. The unique exception to this rule is an azobenzene having a two-carbon bridge between ortho positions, substitutions that lock the photoswitch in its cis configuration. Only thoroughly chemically characterized relatively recently, we describe the first applications of this locked-azobenzene (or "LAB") scaffold with two derivatives designed to control ion flow in pyramidal neurons in acutely isolated brain slices. Our LAB derivatives maintain most of the desirable photochemical properties of the parent scaffold, and work as designed in living cells. However, LAB derivitization changes the trans photostationary state from >85% of the parent photoswitch to about 50%, suggesting that careful design considerations must be given for future applications of the LAB scaffold in biological areas.

SUBMITTER: Thapaliya ER

PROVIDER: S-EPMC6657492 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Locked-Azobenzene: Testing the Scope of a Unique Photoswitchable Scaffold for Cell Physiology.

Thapaliya Ek Raj ER Zhao Jun J Ellis-Davies Graham C R GCR

ACS chemical neuroscience 20190215 5

Azobenzenes are the most widely studied photoswitches, and have become popular optical probes for biological systems. The cis configuration is normally metastable, meaning the trans configuration is always thermodynamically favored. The unique exception to this rule is an azobenzene having a two-carbon bridge between ortho positions, substitutions that lock the photoswitch in its cis configuration. Only thoroughly chemically characterized relatively recently, we describe the first applications o ...[more]

PMID: 30767510

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Project description:In the vast majority of studies on semiconductor particles ligands or capping agents are used that bind to the surface of the particles covering them with an electrically insulating shell. Since the transport of charge carriers and/or energy across interfaces is desirable for a variety of applications, the use of ?-conjugated ligands becomes increasingly interesting. Among them are compounds that react to external stimuli. Molecular switches in particular are fascinating because the properties of the interfaces can be potentially adjusted as required. However, there is debate about how the properties of such special ligands are influenced by the presence of a semiconductor and vice versa. Here ammonium-modified azobenzene compounds were selected as prototypes for molecular switches and organic-inorganic hybrid perovskites as semiconductor materials. The class of ammonium-lead-halide phases as prototypes is peculiar because, in addition to the surface functionalization of 3D crystals, organic compounds can actually be incorporated into the crystal as 2D phases. Thus, for example, layered Ruddlesden-Popper phases are obtained. We present photoswitchable azobenzene ligands with different head-group lengths for the synthesis of 2D and 3D hybrid perovskite phases. The energy transfer mechanisms are influenced by the length of the molecular spacer moiety, which determines the distance between the ? system and the semiconductor surfaces. We find huge differences in the photoswitching behaviour between the free, surface-coordinated and integrated ligands between the perovskite layers. Photoswitching of azobenzene ligands incorporated in 2D phases is nearly quenched, while the same mechanism for surface-coordinating ligands is greatly improved, compared to the free ligands. The improvement originates from an energy transfer from perovskite to azobenzene, which is strongly distance-dependent. This study provides evidence for the photoswitching of azobenzenes as ligands of hybrid perovskites, which depends on the spacing between the chromophore and the perovskite phase.

Dataset Information

Locked-Azobenzene: Testing the Scope of a Unique Photoswitchable Scaffold for Cell Physiology.

Publications

Locked-Azobenzene: Testing the Scope of a Unique Photoswitchable Scaffold for Cell Physiology.

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