Synthesis of a photochromic benzothiazolinic spiropyran

Guglielmetti, R.; Meyer, R.; Dupuy, Charles

doi:10.1021/ed050p413

Cited by 17 publications

(11 citation statements)

References 9 publications

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“…The compounds 2, 7 and 8 were synthesized according to the procedure reported in Guglielmetti et al [19]. The procedure was adapted to synthesize compound 1 as described below and in Scheme 1.…”

Section: Experimental and Computationalmentioning

confidence: 99%

X-ray, kinetics and DFT studies of photochromic substituted benzothiazolinic spiropyrans

Kumar

Velasco

McCurdy

2010

Journal of Molecular Structure

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Photochromic molecules have the potential to find utility in a wide variety of applications including photoswitchable binding and optical memory. This work explores the relationship between photochromism and structural parameters such as particular bond lengths for this class of compounds for which very few crystal structures have been published. Photochemical kinetics, Density Functional Theory (DFT) and X-ray crystallography were used to study the benzothiazolinic spiropyran 3-methyl-6-nitro-3′-methylspiro-[2H-l-benzopyran-2,2′-benzothiazoline]. A second benzothiazolinic spiropyran 3-methyl-8-methoxy-6-nitro-3′-methylspiro-[2H-l-benzopyran-2,2′-benzothiazoline] was synthesized and subjected to photochemical and computational studies. Selected structural and photochemical data for these, related benzothiazolinic spirooxazines and spiropyrans, and related thiazolidinic spiropyrans are compared. Both benzothiazolinic spiropyrans exhibit photochromic properties that are influenced by substituents, solvent, and temperature. The crystallographic C spiro -O bond distance of 3-methyl-6-nitro-3′-methylspiro-[2H-l-benzopyran-2,2′-benzothiazoline] that has been shown to correlate with photochromic properties is 1.458 Å. The crystallographic C spiro -O bond distance matches that of the structure generated by DFT calculations exactly. The effect of substituents on calculated bond lengths and photochemical parameters was determined. For this class of compounds, both X-ray geometry and DFT optimized geometry may be used to predict photochromism, but not degree of photocolorability.

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Section: Experimental and Computationalmentioning

confidence: 99%

X-ray, kinetics and DFT studies of photochromic substituted benzothiazolinic spiropyrans

Kumar

Velasco

McCurdy

2010

Journal of Molecular Structure

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“…The surprise is that the chemistry ones are complex and related to a specific field of organic chemistry called "photochromism" (reproduced in Figure 5a) and a chemical reaction describing the light-induced coloration of a dye belonging to the spiropyran family is clearly visible. 144 Photochromic dyes are commonly used in sunglasses to adapt the optical density of the lenses to the surrounding luminosity. However, spiropyran dyes are rather unstable and fade away readily when used intensively.…”

Section: Rabbids Invasionmentioning

confidence: 99%

Using Pop-Culture to Engage Students in the Classroom

et al. 2021

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Herein, we describe how video games, TV shows or movies have been used to provide an innovative framework for students to think about chemistry and chemical engineering.The main objective of this paper is to show how science can be linked with pop culture, to provide educators with recent materials to use in classrooms, and to discuss the benefits and limitations of such tools. The videogames Fortnite, Spiderman and Angry Birds, the TV shows Game of Thrones and Breaking Bad, the Marvel movies, and the animated programs Raving Rabbids and Dragon Ball are used to illustrate different approaches to engage with students and encourage them to learn in a more recreational environment.

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“…In order to demonstrate and investigate the photochromism of a photoactive molecular switch and to address a considerable number of photochemical concepts, we use the non‐hazardous and commercially available spiropyran (1,3,3‐trimethylindolino‐6’‐nitrobenzopyrylospirane; SP), which has been known for more than 60 years [17] . One of us has been dealing with this compound for more than 30 years, and other authors have also reported in educational journals about experiments with spiropyran [18–20] . The experimental observations listed below can be carried out easily as microscale versions using solutions of approx.…”

Section: Spiropyran/merocyanine: a “Dream Couple” For Teaching Core C...mentioning

confidence: 99%

Teaching Photochemistry: Experimental Approaches and Digital Media

et al. 2021

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In this paper we give an insight into results from our curricular innovation research which aims at integrating photochemistry in university and school curricula. We have been exploring experimental approaches and developing teaching materials for more than 20 years and most of our experiments and teaching materials have been digitalized and made available in German and English as open educational resources (OER) on our website. The addressed photochemical content can be connected to well‐established subject content at school and university level chemistry, but their theoretical interpretation and the understanding of their applications go well beyond this. However, primarily they should motivate learners to, even after they leave school and university, continue to work on the investigation and development of sustainable processes and materials based on the use of (solar) light.

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Synthesis of a photochromic benzothiazolinic spiropyran

Abstract: The purpose of this type of experiment is to elucidate structure of the different compounds gradually prepared starting from reaction mechanisms and chiefly from spectroscopic data given perviously to students.

Cited by 17 publications

References 9 publications

X-ray, kinetics and DFT studies of photochromic substituted benzothiazolinic spiropyrans

X-ray, kinetics and DFT studies of photochromic substituted benzothiazolinic spiropyrans

Using Pop-Culture to Engage Students in the Classroom

Teaching Photochemistry: Experimental Approaches and Digital Media

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