Recent advance of photochromic diarylethenes-containing supramolecular systems

Xiao, Chao; Zhao, Wei‐Ye; Zhou, Da‐Yang; Huang, Yan; Ye, Tao; Wu, Wanhua; Yang, Cheng

doi:10.1016/j.cclet.2015.05.013

Cited by 35 publications

(17 citation statements)

References 52 publications

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“…They are also responsive in the solid state. [14][15][16][17] DTEs have been discussed as functional key componentsi narange of applications including conductive polymers, [18] multiresponsive molecular switches, [19] optical memory devices, [20] photoresponsive buildingb locks that can regulate supramolecular architectures, [21,22] as electivef luorescent probe for the detection of metal ions, [23] and photoresponsive self-assemblies at liquidsolid interfaces. [24] DTE derivatives that show turn-on mode fluorescencea re promising candidates for applicationsi n super-resolutionf luorescencem icroscopy [24] and all-optical transistors.…”

Section: Introductionmentioning

confidence: 99%

Non‐Oxido‐Vanadium(IV) Metalloradical Complexes with Bidentate 1,2‐Dithienylethene Ligands: Observation of Reversible Cyclization of the Ligand Scaffold in Solution

Schlüter

Kleemiss

Fugel

et al. 2020

Chemistry A European J

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Derivatives of 1,2-dithienylethene (DTE)h ave superb photochromic properties due to an efficient reversible photocyclization reaction of their hexatriene structure and, thus, have application potential in materials for optoelectronics and (multi-responsive) molecular switches. Transition-metal complexes bearing switchable DTE motifsc ommonly incorporate their coordination site ratherd istantf rom the hexatriene system.I nt his work the redoxa ctive ligand 1,2-bis(2,5-dimethylthiophen-3-yl)ethane-1,2-dione is described,w hich reacts with [V(TMEDA) 2 Cl 2 ]t og ive ar are nonoxido vanadium(IV) species 3(M,M/P,P).T his blue complex has two bidentate en-diolato ligandsw hich chelate the V IV center and give rise to two five-membered metallacycles with the adjacent hexatriene DTE backboneb earing axial chirality.U pon irradiation with UVAl ight or prolonged heating in solution, the blue compound 3(M,M/P,P) converts into the purple atropisomer 4(para,M/para,P).B othc omplexes were isolated and structurally characterized by single-crystal X-ray diffraction analysis (using lab source and synchrotron radiation). The antiparallel configuration( M or P helicity) present in both 3(M,M/P,P) and 4(para,M/para,P) is aprerequisite for (reversible)6 p cyclization reactions. AC WE PR spectroscopic study reveals the metalloradical character for 3(M,M/P,P) and 4(para,M/para,P) and indicatesd ynamic reversible cyclization of the DTE backbonei nc omplex 3(M,M/ P, P ) at ambient temperature in solution.

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Section: Introductionmentioning

confidence: 99%

Non‐Oxido‐Vanadium(IV) Metalloradical Complexes with Bidentate 1,2‐Dithienylethene Ligands: Observation of Reversible Cyclization of the Ligand Scaffold in Solution

Schlüter

Kleemiss

Fugel

et al. 2020

Chemistry A European J

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“…In this paper, we present a new strategy for improving TTA-UC through host–guest complexation (Figure b) . Our central hypothesis is that TTET should be facilitated by positioning the sensitizer and emitter in close proximity through host–guest complexation, and intramolecular singlet back energy transfer should be avoided because the sensitizer and the emitter are brought in close proximity by noncovalent interactions.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Triplet–Triplet Energy Transfer and Upconversion Fluorescence through Host–Guest Complexation

et al. 2016

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Perylene-tethered pillar[5]arenes and C-boron-dipyrromethene (BODIPY) dyads were synthesized acting as emitters and organic triplet photosensitizers, respectively, for the purpose of improving the efficiency of triplet-triplet annihilation upconversion (TTA-UC). The photophysical properties of the sensitizers (guests) and the emitters (hosts) were not greatly influenced by the chemical modifications except for a notable decrease in the fluorescence quantum yields of the perlyene emitters due to the high local concentration. The perylene-tethered pillar[5]arenes form stable 1:1 complexes with a nitrile-bearing C-BODIPY dyad, showing association constants as high as 4.0 × 10 M. Through host-guest complexation, the efficiencies of both triplet-triplet energy transfer and TTA were significantly enhanced, which overcompensated for the loss of the fluorescence quantum yield of the emitters (hosts). Thus, an improved TTA-UC efficiency of 3.2% was observed even at a diluted concentration of 6 × 10 M, demonstrating for the first time the effectiveness of the supramolecular motif for enhancing TTA-UC without varying the inherent photophysical properties of sensitizers and emitters.

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“…Unsubstituted buckybowls 1 and 2 are not chiral due to the presence of the reflection symmetry with respect to the mirror planes containing the rotational axis to show C 5v and C 3v symmetry, respectively. Introducing the addends may break the reflection symmetry to cause chirality, and alter their properties, such as bowl-to-bowl inversion [12][13][14][15][16][17][18][19][20][21][22], chirality [12,17,19,23], bowl depth [14,19,20], crystal structure [19,24,25], molecular recognition [2,26,27,51] and supramolecular assembly [3,[28][29][30]52,53] behavior, metal complexation [23,[31][32][33][34][35][36], electronic conductivity [19,37,38], and so on. Although the chirality is an important element in three-dimensional curved π-electron systems, thus far there have been no reports of the enantioselective synthetic control of the bowl chirality.…”

Section: Stereodescriptor System Of Buckybowlsmentioning

confidence: 99%

Chiral Buckybowl Molecules

Kanagaraj

Lin

et al. 2017

Symmetry

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Buckybowls are polynuclear aromatic hydrocarbons that have a curved aromatic surface and are considered fragments of buckminsterfullerenes. The curved aromatic surface led to the loss of planar symmetry of the normal aromatic plane and may cause unique inherent chirality, so-called bowl chirality, which it is possible to thermally racemize through a bowl-to-bowl inversion process. In this short review, we summarize the studies concerning the special field of bowl chirality, focusing on recent practical aspects of attaining diastereo/enantioenriched chiral buckybowls through asymmetric synthesis, chiral optical resolution, selective chiral metal complexation, and chiral assembly formation.

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Recent advance of photochromic diarylethenes-containing supramolecular systems

Cited by 35 publications

References 52 publications

Non‐Oxido‐Vanadium(IV) Metalloradical Complexes with Bidentate 1,2‐Dithienylethene Ligands: Observation of Reversible Cyclization of the Ligand Scaffold in Solution

Non‐Oxido‐Vanadium(IV) Metalloradical Complexes with Bidentate 1,2‐Dithienylethene Ligands: Observation of Reversible Cyclization of the Ligand Scaffold in Solution

Enhanced Triplet–Triplet Energy Transfer and Upconversion Fluorescence through Host–Guest Complexation

Chiral Buckybowl Molecules

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