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Rationalization of the color properties of fluorescein in the solid state: a combined computational and experimental study

Rationalization of the color properties of fluorescein in the solid state: a combined computational and experimental study
Rationalization of the color properties of fluorescein in the solid state: a combined computational and experimental study
Fluorescein is known to exist in three tautomeric forms defined as quinoid, zwitterionic and lactoid. In the solid state, the quinoid and zwitterionic forms give rise to red and yellow materials respectively. The lactoid form has not been crystallized pure, although its cocrystal and solvate forms exhibit colors ranging from yellow to green. An explanation for the observed colors of the crystals is found using a combination of UV/Vis spectroscopy and plane-wave DFT calculations. In addition, the role of cocrystal coformers in modifying crystal color is established. Several new crystal structures are determined using a combination of X-ray and electron diffraction, solid-state NMR and crystal structure prediction (CSP). The protocol presented herein may be used to predict color properties of materials prior to their synthesis.
0947-6539
10065-10073
Arhangelskis, Mihails
33bdbac5-369b-41f9-aef6-eb7fe518745b
Eddleston, Mark D.
01211ad8-8115-43de-914c-6501d1d4c584
Reid, David G.
0d06f1c4-82d5-4c93-af16-92e236df84e7
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636
Bucar, Dejan-Kresimir
bc6773f5-d0fc-453a-ace7-e4f969fae8b4
Morris, Andrew J.
7b27a3f0-6110-453a-90d2-e087eb9a5fd0
Jones, William
3173abf0-1cfa-45f0-996e-2586b385c21e
Arhangelskis, Mihails
33bdbac5-369b-41f9-aef6-eb7fe518745b
Eddleston, Mark D.
01211ad8-8115-43de-914c-6501d1d4c584
Reid, David G.
0d06f1c4-82d5-4c93-af16-92e236df84e7
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636
Bucar, Dejan-Kresimir
bc6773f5-d0fc-453a-ace7-e4f969fae8b4
Morris, Andrew J.
7b27a3f0-6110-453a-90d2-e087eb9a5fd0
Jones, William
3173abf0-1cfa-45f0-996e-2586b385c21e

Arhangelskis, Mihails, Eddleston, Mark D., Reid, David G., Day, Graeme M., Bucar, Dejan-Kresimir, Morris, Andrew J. and Jones, William (2016) Rationalization of the color properties of fluorescein in the solid state: a combined computational and experimental study. Chemistry - A European Journal, 22 (29), 10065-10073. (doi:10.1002/chem.201601340).

Record type: Article

Abstract

Fluorescein is known to exist in three tautomeric forms defined as quinoid, zwitterionic and lactoid. In the solid state, the quinoid and zwitterionic forms give rise to red and yellow materials respectively. The lactoid form has not been crystallized pure, although its cocrystal and solvate forms exhibit colors ranging from yellow to green. An explanation for the observed colors of the crystals is found using a combination of UV/Vis spectroscopy and plane-wave DFT calculations. In addition, the role of cocrystal coformers in modifying crystal color is established. Several new crystal structures are determined using a combination of X-ray and electron diffraction, solid-state NMR and crystal structure prediction (CSP). The protocol presented herein may be used to predict color properties of materials prior to their synthesis.

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Accepted/In Press date: 5 May 2016
e-pub ahead of print date: 15 June 2016
Published date: 11 July 2016
Organisations: Chemistry

Identifiers

Local EPrints ID: 393839
URI: https://eprints.soton.ac.uk/id/eprint/393839
ISSN: 0947-6539
PURE UUID: 47880634-4489-4a7d-8357-e7c3f1855f64
ORCID for Graeme M. Day: ORCID iD orcid.org/0000-0001-8396-2771

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Date deposited: 10 May 2016 10:23
Last modified: 15 Aug 2019 05:30

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Contributors

Author: Mihails Arhangelskis
Author: Mark D. Eddleston
Author: David G. Reid
Author: Graeme M. Day ORCID iD
Author: Dejan-Kresimir Bucar
Author: Andrew J. Morris
Author: William Jones

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