Supramolecular control of photochromism in a β-cyclodextrin/Schiff base system

Hadjoudis, E.; Yannakopoulou, Konstantina; Chatziefthimiou, Spyros D.; Paulidou, Anastasia; Mavridis, Irene M.

doi:10.1016/j.jphotochem.2010.10.022

Cited by 22 publications

(11 citation statements)

References 14 publications

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“…[ 1 ] Among these, much of the polymer backbone, and lower aggregation tendency. [11][12][13][14][15][16][17][18][19][20] The encapsulation into macrocyclic cavities, i.e., native cyclodextrins (CDs) of PAMs present noticeable advantages for optoelectronic applications, compared to those observed on nonrotaxane counterparts, due to easier processability and adhesivity on the substrates of solid fi lms, as well as the improvements of morphological characteristics. [ 16,17,19,21,22 ] The use of permodifi ed CDs derivatives, which exhibit higher solubility in nonpolar organic solvents and lower propensity to aggregate formations [ 23,24 ] has been employed as an alternative supramolecular approach for the synthesis of polyrotaxanes with conjugated polymers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Photophysical, and Morphological Properties of Azomethine‐Persylilated α‐Cyclodextrin Main‐Chain Polyrotaxane

Farcas¹,

Resmeriță²,

Aubert

et al. 2015

Macro Chemistry & Physics

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The synthesis of 2-rotaxane (3•TMS-αCD) through a condensation reaction between 3,5-diamino-1,2,4-triazole encapsulated into hexakis(2,3,6-trimethylsilyl) α-cyclodextrin cavity (TMS-αCD ) and 1-pyrenecarboxaldehyde is reported. The oxidative coupling of 3•TMS-αCD afforded then pyrene-triazole/TMS-αCD PAMs polyrotaxane (4•TMS-αCD) azomethine polyrotaxane. The optical, electrochemical, morphological, surface-free energies, as well as transport properties of 3•TMS-αCD and its corresponding 4•TMS-αCD polyrotaxane have been investigated and compared with those of the reference polymer pyrene-triazole azomethine. The polyrotaxane is soluble in toluene/dimethylformamide (DMF) 1:1, v/v, mixture and displays useful levels of thermal stability and higher fl uorescence quantum yield ( Φ PL ) in DMF solutions. Φ PL improvement is further refl ected in the fl uorescence lifetime ( τ F ), signifi cantly longer than that of the starting monomer 3•TMS-αCD (7.8 vs 0.89 ns). In addition, a smoother surface with the smaller grains uniformly distributed on the surface, as well as lower surface-free energy, combined with energy gap (3.32 vs 3.76 eV) represent noticeable advantages of azomethine backbones encapsulation by TMS-αCD.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Photophysical, and Morphological Properties of Azomethine‐Persylilated α‐Cyclodextrin Main‐Chain Polyrotaxane

Farcas¹,

Resmeriță²,

Aubert

et al. 2015

Macro Chemistry & Physics

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“…Numerous trials to crystallize the inclusion complex of β-CD with D-NAcTrp have failed to give anything but hydrated β-CD crystals [ 29 ], as described in detail in the experimental section, however, some crystals were grown after hydrothermal treatment of the solution (65 °C for duration of 6 days) [ 30 – 31 ]. The structure of the latter could not be solved by isomorphous replacement (using the coordinates of β-CD–glutaric acid complex [ 32 ], that is isomorphous to hydrated β-CD [ 29 ].…”

Section: Resultsmentioning

confidence: 99%

Molecular recognition of N-acetyltryptophan enantiomers by β-cyclodextrin

Chatziefthimiou¹,

Inclán²,

Giastas³

et al. 2017

Beilstein J. Org. Chem.

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The enantioselectivity of β-cyclodextrin (β-CD) towards L- and D-N-acetyltryptophan (NAcTrp) has been studied in aqueous solution and the crystalline state. NMR studies in solution show that β-CD forms complexes of very similar but not identical geometry with both L- and D-NAcTrp and exhibits stronger binding with L-NAcTrp. In the crystalline state, only β-CD–L-NAcTrp crystallizes readily from aqueous solutions as a dimeric complex (two hosts enclosing two guest molecules). In contrast, crystals of the complex β-CD–D-NAcTrp were never obtained, although numerous conditions were tried. In aqueous solution, the orientation of the guest in both complexes is different than in the β-CD–L-NAcTrp complex in the crystal. Overall, the study shows that subtle differences observed between the β-CD–L,D-NAcTrp complexes in aqueous solution are magnified at the onset of crystallization, as a consequence of accumulation of many soft host–guest interactions and of the imposed crystallographic order, thus resulting in very dissimilar propensity of each enantiomer to produce crystals with β-CD.

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“…Furthermore, the benzene ring and C=N formed conjugated system and the whole molecule became more stable. So the proton transfer could take place [20,[22][23][24][25][26][27][28][29].…”

Section: The Effect Of Substituents On Thermochromism or Photochromismmentioning

confidence: 99%

Synthesis, Characterization, Thermochromism, and Photochromism of Aromatic Aldehyde Hydrazone Derivatives

Zhu

Chen

Sun

et al. 2016

Journal of Chemistry

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The Schiff bases N-(5-phenylthiazole-2-yl)-2-hydroxylnaphthaldehydehydrazone (1), N-(4′-chloro-5-phenylthiazole-2-yl)-2-hydroxylnaphthaldehydehydrazone (2), and N-(4′-nitro-5-phenylthiazole-2-yl)-2-hydroxylnaphthaldehydehydrazone (3) were synthesized. These compounds were characterized by using IR,1H NMR,13C NMR, and MS. The photochromism of the compounds was investigated by IR and UV-visible spectrometry which is time variable under irradiation of 254 nm UV light. The thermochromism of the compounds was studied using temperature-variable IR, UV-visible spectrometry, TG, and differential scanning calorimetry (DSC). The results suggested that compound2showed thermochromism properties and compounds2and3displayed photochromism properties. The relationship between the substituents species and photochromic or thermochromic properties of these compounds was revealed as well.

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Supramolecular control of photochromism in a β-cyclodextrin/Schiff base system

Cited by 22 publications

References 14 publications

Synthesis, Photophysical, and Morphological Properties of Azomethine‐Persylilated α‐Cyclodextrin Main‐Chain Polyrotaxane

Synthesis, Photophysical, and Morphological Properties of Azomethine‐Persylilated α‐Cyclodextrin Main‐Chain Polyrotaxane

Molecular recognition of N-acetyltryptophan enantiomers by β-cyclodextrin

Synthesis, Characterization, Thermochromism, and Photochromism of Aromatic Aldehyde Hydrazone Derivatives

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