volume 1 issue 14 pages 3259-3267

Proton exchange and isomerisation reactions of photochromic and reverse photochromic spiro-pyrans and their merocyanine forms

Jonathan Hobley
Vincenzo Malatesta
Roberto Millini
L Montanari
W. O. Parker
Publication typeJournal Article
Publication date1999-01-01
scimago Q2
wos Q2
SJR0.698
CiteScore5.3
Impact factor2.9
ISSN14639076, 14639084
Physical and Theoretical Chemistry
General Physics and Astronomy
Abstract
Photochromic 1′,3′,3′-trimethyl-6,8-dinitro-spiro- [2H-1-benzopyran-2,2-indoline], (6,8-dinitro BIPS) has been studied in different solvents using 1H-NMR techniques, UV/visible spectroscopy, X-ray diffraction and electrospray ionisation mass spectroscopy (ESI-MS). Molar decadic absorption coefficients for 6,8-dinitro BIPS were found to range between 35000–45000 d mol-1 cm-1. 1H–1H NOESY and 1H-NMR experiments have established that in solution the merocyanine form of 6,8-dinitro BIPS is in rapid exchange between the trans-trans-cis (TTC) and trans-trans-trans (TTT) isomers. The 3B proton on the central bridging double bond of spiro-pyran merocyanines is labile in organic solvents. The closed form of 6,8-dinitro BIPS enantiomerises about the spiro C(2) carbon at a rate of 18 s-1 at 300 K. The activation energy for this process was estimated to be 46 kJ mol-1 using dynamic NMR.
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Hobley J. et al. Proton exchange and isomerisation reactions of photochromic and reverse photochromic spiro-pyrans and their merocyanine forms // Physical Chemistry Chemical Physics. 1999. Vol. 1. No. 14. pp. 3259-3267.
GOST all authors (up to 50) Copy
Hobley J., Malatesta V., Millini R., Montanari L., Parker W. O. Proton exchange and isomerisation reactions of photochromic and reverse photochromic spiro-pyrans and their merocyanine forms // Physical Chemistry Chemical Physics. 1999. Vol. 1. No. 14. pp. 3259-3267.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1039/a902379h
UR - https://doi.org/10.1039/a902379h
TI - Proton exchange and isomerisation reactions of photochromic and reverse photochromic spiro-pyrans and their merocyanine forms
T2 - Physical Chemistry Chemical Physics
AU - Hobley, Jonathan
AU - Malatesta, Vincenzo
AU - Millini, Roberto
AU - Montanari, L
AU - Parker, W. O.
PY - 1999
DA - 1999/01/01
PB - Royal Society of Chemistry (RSC)
SP - 3259-3267
IS - 14
VL - 1
SN - 1463-9076
SN - 1463-9084
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{1999_Hobley,
author = {Jonathan Hobley and Vincenzo Malatesta and Roberto Millini and L Montanari and W. O. Parker},
title = {Proton exchange and isomerisation reactions of photochromic and reverse photochromic spiro-pyrans and their merocyanine forms},
journal = {Physical Chemistry Chemical Physics},
year = {1999},
volume = {1},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://doi.org/10.1039/a902379h},
number = {14},
pages = {3259--3267},
doi = {10.1039/a902379h}
}
MLA
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MLA Copy
Hobley, Jonathan, et al. “Proton exchange and isomerisation reactions of photochromic and reverse photochromic spiro-pyrans and their merocyanine forms.” Physical Chemistry Chemical Physics, vol. 1, no. 14, Jan. 1999, pp. 3259-3267. https://doi.org/10.1039/a902379h.