Photochromic behavior of spiropyran in polymer matrices

Tork, Amir; Boudreault, Francois; Roberge, Mathieu; Ritcey, Anna M.; Lessard, Roger A.; Galstian, Tigran

doi:10.1364/ao.40.001180

Cited by 60 publications

(47 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…On the other hand, they noticed that when the concentration of SP in the film was reduced, the degree of photodegradation also reduced, implying that aggregation of MC also has important role in the photodegradation process. A similar conclusion was drawn by Arai et al and Tork et al while studying photodegradation of MC in solution 29 and polymer matrixes, 30 respectively. The work of these research groups indicates that reducing the degree of motion of MC reduces the possibility of interaction between MC molecules and has beneficial effects on reducing the photo-fatigue.…”

Section: Photodegradation the Results Presented Insupporting

confidence: 84%

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

Radu

Byrne

Alhashimy

et al. 2009

Journal of Photochemistry and Photobiology A: Chemistry

View full text Add to dashboard Cite

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

show abstract

Section: Photodegradation the Results Presented Insupporting

confidence: 84%

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

Radu

Byrne

Alhashimy

et al. 2009

Journal of Photochemistry and Photobiology A: Chemistry

View full text Add to dashboard Cite

show abstract

“…4,4'-dihydroxybiphenyl-3,3'-dicarbaldehyde (1), 24 5-iodo-2,3,3-trimethyl-3H-indole (3), 25 3,3'-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-ethynyl-2-methylthiophene) (6) 26 were obtained by following procedures reported elsewhere. All commercially available materials were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

“…[4][5][6][7][8][9][10][11][12][13][14][15] However, the synthesis and characterization of oligomers or polymers containing spiropyran moieties in the main backbone have not been well investigated. [16][17][18][19][20][21][22][23] Herein, we report the synthesis and characterization of conjugated bis-spiropyran derivatives.…”

mentioning

confidence: 99%

Synthesis and Characterizations of Bis-Spiropyran Derivatives

Lee¹,

Ji²,

Kang³

2012

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

We synthesized three different derivatives of bis-spiropyran using simple organic reactions with high yields. BSP1, a derivative of bis-spiropyran having a connection at the position 6' and BSP2, a derivative of bisspiropyran having a connection at the position 5 and BSP3, a derivative of bis-spiropyran containing a dithienylethene group between two spiropyran moieties were synthesized. The optical properties of BSPs were characterized. UV-Vis spectra showed that BSPs exhibit reversible photo-isomerization and the efficiency of photo-isomerization is highly dependent on the position of nitro group. BSPs having nitro group at para position of hydroxy group showed the higher efficiency of photo-isomerization that the one having nitro group at ortho position. The optical microscope images obtained under ultraviolet or visible light exposure demonstrated that the formation of nanorods can be reversibly controlled by optical signal.

show abstract

“…One of the characteristic features of spiropyrans is a strong absorption, maximum around the 290-380 nm regions due to the presence of benzopyran moiety. A number of attempts to incorporate spiropyran molecules into polymer systems have been reported, which include photochromic studies of spiropyrans in polymer matrices [62], liquid crystal polymers containing spiropyran as mesophases [63], and spiropyran-grafted dextran [64], pullulan [65], polydimethylsiloxane [66], and other synthetic polymers [67]. Selected examples are illustrated in Figure 9.6.…”

Section: Spiropyransmentioning

confidence: 99%

Photochromic Responses in Polymer Matrices

Ramachandran

Urban

2011

Handbook of Stimuli‐Responsive Materials

View full text Add to dashboard Cite

IntroductionMany concepts of photochromic systems have been inspired by nature. An illustrative example is the reversible shape changes of the photoreceptor molecule rhodopsin in eyes that produces a cascade of molecular rearrangements responding to light illumination [1]. Upon photoexcitation, all-trans retinal undergoes isomerization to 11-cis across the double bond, thus causing shape changes. Although this event occurs at the angstrom (Å) level, there are many molecular interconnected events and responses that are not fully understood. Similar processes have been observed in certain molecules in materials chemistry, although on a much smaller and at a less-orchestrated scale. These are known as photochromic molecules, which were discovered over 150 years ago in an organic crystal of tetracene, and later on, in inorganic and organometallic materials [2][3][4]. In spite of a long research history, a quest for new photochromic materials continues. Color changes induced by ultraviolet (UV) radiation caused by trans − − cis isomerization, ring opening-closing reactions, inter-or intramolecular charge transfer, or bimolecular cycloaddition reactions are of particular interest. To make use of their photochromic behavior in various applications, photochromic entities are often incorporated into polymer matrices.While creating individual molecules and understanding their electronic properties facilitated further advances in understanding molecular mechanisms governing photochromism, useful applications require fabrication into films, sheets, fibers, or beads. This is typically achieved by incorporating photochromic molecules into macromolecular matrices by doping or dispersing, or covalently attaching them onto a polymer backbone. Since photoisomerization of chromophores alter equilibrium conformations, the dimensions of the surrounding polymer matrix play an essential role in spatial rearrangements. The dimensional classifications of the matrix effect have been extensively examined [5], with notable applications in ophthalmic lens, optical storage media, photosensors, and biomedical devices. Furthermore, the kinetics of conformational changes of polymers with photochromic moieties depends upon their physical or chemical incorporation into the matrix [6]. As one Handbook of Stimuli-Responsive Materials. Edited by Marek W. Urban

show abstract

Photochromic behavior of spiropyran in polymer matrices

Cited by 60 publications

References 10 publications

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

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

Synthesis and Characterizations of Bis-Spiropyran Derivatives

Photochromic Responses in Polymer Matrices

Contact Info

Product

Resources

About