Photochromism of a spiropyran derivative of 1,3-calix[4]crown-5

Grofcsik, A.; Baranyai, Péter; Bitter, István; Grűn, Alajos; Kőszegi, Éva; Kubinyi, Miklós; Pál, Krisztina; Vidóczy, Tamás

doi:10.1016/s0022-2860(02)00242-9

Cited by 21 publications

(9 citation statements)

References 16 publications

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“…However, several research groups have developed ligands based on placement of additional binding groups typically at the ortho position relative to the MC phenolate ion. 11, [31][32][33] In this work, we have adopted a similar approach and synthesized a methoxy derivative as shown in Figure 1. It is expected that addition of this additional electron withdrawing group should increase the charge density on the phenolate ion and also create another oxygen binding centre for multivalent ions.…”

Section: Photodegradation the Results Presented Inmentioning

confidence: 99%

Spiropyran-based reversible, light-modulated sensing with reduced photofatigue

Radu

Byrne

Alhashimy

et al. 2009

Journal of Photochemistry and Photobiology A: Chemistry

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Switchable materials have tremendous potential for application in sensor development that could be applied to many fields. We are focusing on emerging area of wireless sensor networks due to the potential impact of this concept in society. Spiropyran-based sensors are probably the most studied type of photoswitchable sensing devices. They suffer from many issues but photofatigue, insufficient selectivity and lack of sensitivity are probably the most important characteristics that hinder their wider application. Here, we are address these issues and demonstrate that covalent attachment of modified spiropyran into a polymeric film significantly reduces photodegradation. The observed signal loss after 12 th cycle of switching between the spiropyran and merocyanine forms is only about 27% compared to the loss of 57% of the initial signal in an equivalent experiment based on nonimmobilized spiropyran. This has enabled us to demonstrate at least 5 reversible cycles of detection of an ion of interest (in our case H + ) with minimal signal loss. Furthermore, we demonstrate that the sensitivity can be increased by incorporation of additional binding groups in the parent spiropyran molecule. Using molecular modeling to calculate the relevant bond lengths as a measure of interaction between MC and H + , the calculated increase of H-bond strength is approximately an order of magnitude for a derivative containing a methoxy group incorporated in the o-position of the parent spiropyran in comparison to the equivalent unsubstituted phenol. This theoretical result was found to correspond very well with experimental observation. As a result, we have increased the sensitivity to H + by approximately one order of magnitude.3

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Section: Photodegradation the Results Presented Inmentioning

confidence: 99%

Spiropyran-based reversible, light-modulated sensing with reduced photofatigue

Radu

Byrne

Alhashimy

et al. 2009

Journal of Photochemistry and Photobiology A: Chemistry

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“…SP-1 is an important model of spiropyran type photochromic compounds [10][11][12][13][14][15][16][17]. Various derivatives of SP-1 have been synthesized that form complexes of high stability with metal ions, like the 'bidentate' ligands (they bridge the metal ion by the phenolic oxygen of their MC form and an additional receptive site) [18,19], the multidentate ligands [20,21] and the spiropyrans with attached macrocyclic coordination spheres [22][23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Metal complexes of the merocyanine form of nitrobenzospyran: Structure, optical spectra, stability

Kubinyi

Varga

Baranyai

et al. 2011

Journal of Molecular Structure

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“…11,12 Reverse photochromism has been attributed to the stabilization of the MC form via hydrogen bonding with the microenvironment around the molecule. 11,13 A way to retain or adapt the physical-chemical properties of the spiropyrans can be by its molecular encapsulation in an appropriate matrix, 14 by chemical structural modification or non-covalently doping of the molecule into appropriate matrices such as polymers [15][16][17] or cyclodextrin (CD) cavity. 5,12 CDs have a rigid and well defined structure with a hydrophobic cavity.…”

Section: Introductionmentioning

confidence: 99%

Photo-response behavior of electrospun nanofibers based on spiropyran-cyclodextrin modified polymer

Sousa

Guerreiro

et al. 2010

J. Mater. Chem.

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Tunable and durable photochromic materials are a rapidly expanding area of interest, with applications ranging from biomedical devices to industrial-fields. Here we examine electrospun poly (methacrylic acid) PMAA nanofibers covalently modified with the highly photochromic molecule, spiropyran (SP) or a derivate SP which is firstly coupled to a cyclodextrin molecule (βCDSP). The photochromic properties of the starting materials and of the nanofibers were investigated. βCDSP, PMAASP and PMAA-βCDSP polymers exhibited a reverse photochromism. The kinetic results revealed a faster isomerization process for the βCDSP molecule, than that for the PMAA-βCDSP and for the PMAASP, the slowest one. The fastest isomerization is attributed to the presence of a large number of hydroxyl groups of the βCD which stabilizes the merocyanine form via hydrogen bonding, and the slowest isomerization is related to the PMAA chain structure that stabilizes the spiropyran form. Thus, combining the PMAA and βCD properties the photo-isomerization can be modulated. The photoreversibility of this material was verified by UV-visible measurements cycling visible and UV light. Infrared spectroscopy and water contact angle were used for the nanofiber surface characterization, demonstrating the presence of the spiropyran on the mats surface and also showing a minimal effect on nanofiber size and shape when compared to PMAA fiber.

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Photochromism of a spiropyran derivative of 1,3-calix[4]crown-5

Cited by 21 publications

References 16 publications

Spiropyran-based reversible, light-modulated sensing with reduced photofatigue

Spiropyran-based reversible, light-modulated sensing with reduced photofatigue

Metal complexes of the merocyanine form of nitrobenzospyran: Structure, optical spectra, stability

Photo-response behavior of electrospun nanofibers based on spiropyran-cyclodextrin modified polymer

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