Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines
Edward I Balmond
1
,
Brandon K Tautges
1
,
Andrea L Faulkner
1
,
Victor W Or
1
,
Blanka M Hodur
1
,
Jared T Shaw
1
,
Angelique Louie
2
Publication type: Journal Article
Publication date: 2016-09-21
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
27529635
Organic Chemistry
Abstract
Spiropyrans and spirooxazines represent an important class of photochromic compounds with a wide variety of applications. In order to effectively utilize and design these photoswitches it is desirable to understand how the substituents affect photochromic properties, and how the different structural motifs compare under identical conditions. In this work a small library of photoswitches was synthesized in order to comparatively evaluate the effect of substituent modifications and structure on photochromism. The library was designed to modify positions that were believed to have the greatest effect on C-O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends in substituent and structural requirements for optimal photochromism.
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Balmond E. I. et al. Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines // Journal of Organic Chemistry. 2016. Vol. 81. No. 19. pp. 8744-8758.
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Balmond E. I., Tautges B. K., Faulkner A. L., Or V. W., Hodur B. M., Shaw J. T., Louie A. Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines // Journal of Organic Chemistry. 2016. Vol. 81. No. 19. pp. 8744-8758.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.6b01193
UR - https://doi.org/10.1021/acs.joc.6b01193
TI - Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines
T2 - Journal of Organic Chemistry
AU - Balmond, Edward I
AU - Tautges, Brandon K
AU - Faulkner, Andrea L
AU - Or, Victor W
AU - Hodur, Blanka M
AU - Shaw, Jared T
AU - Louie, Angelique
PY - 2016
DA - 2016/09/21
PB - American Chemical Society (ACS)
SP - 8744-8758
IS - 19
VL - 81
PMID - 27529635
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2016_Balmond,
author = {Edward I Balmond and Brandon K Tautges and Andrea L Faulkner and Victor W Or and Blanka M Hodur and Jared T Shaw and Angelique Louie},
title = {Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines},
journal = {Journal of Organic Chemistry},
year = {2016},
volume = {81},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.joc.6b01193},
number = {19},
pages = {8744--8758},
doi = {10.1021/acs.joc.6b01193}
}
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Balmond, Edward I., et al. “Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines.” Journal of Organic Chemistry, vol. 81, no. 19, Sep. 2016, pp. 8744-8758. https://doi.org/10.1021/acs.joc.6b01193.