Tuning of switching properties and excited-state dynamics of fulgides by structural modifications

Siewertsen R, Strübe F, Mattay J, Renth F, Temps F (2011)
Physical Chemistry Chemical Physics 13(9): 3800-3808.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Siewertsen, Ron; Strübe, FrankUniBi; Mattay, JochenUniBi; Renth, Falk; Temps, Friedrich
Abstract / Bemerkung
The ultrafast photo-induced dynamics of the E-isomers of four selected photochromic fulgides with distinct structural motifs have been elucidated by femtosecond broadband transient absorption spectroscopy in n-hexane as solvent. E -> C and E -> Z isomerisations, respectively, with time constants of similar to 0.12 +/- 0.02 ps and similar to 0.34 +/- 0.03 ps taking place in parallel were found for derivatives with a methyl substituent at the central hexatriene (HT) unit. In contrast, fulgides with increased steric constraints by an iso-propyl substituent or by intramolecular bridging displayed virtually zero E -> Z isomerisation, but instead a desired accelerated and more efficient ring closure in a reaction time of only similar to 50 +/- 10 fs. Both photoisomerisations appear to follow excited-state pathways with distinctive conical intersections. For the ring closure, direct barrierless pathways with steep downhill gradients are likely. Furthermore, the results indicate conformer-specific reactions, with ring closure exclusively by the E-alpha conformer and E -> Z isomerisation predominantly by the E-beta conformer, because the E-alpha -> Z channel is unfavoured by the faster and kinetically more competitive E-alpha -> C reaction. DFT calculations of the equilibrium structures showed that the sterically demanding groups at the HT unit shift the conformer equilibria towards the E-alpha conformers. At the same time, they appear to cause a favourable pre-orientation of the furyl unit that accelerates the conrotatory ring closure in the E-alpha -> C reaction. Benzo-annulation of the furyl unit has little effect on the observed dynamics. Overall, the results demonstrate how the excited-state dynamics and thereby the photoswitching properties of fulgides can be successfully tuned and improved by structural modifications at the chromophores.
Erscheinungsjahr
2011
Zeitschriftentitel
Physical Chemistry Chemical Physics
Band
13
Ausgabe
9
Seite(n)
3800-3808
ISSN
1463-9076
eISSN
1463-9084
Page URI
https://pub.uni-bielefeld.de/record/2094416

Zitieren

Siewertsen R, Strübe F, Mattay J, Renth F, Temps F. Tuning of switching properties and excited-state dynamics of fulgides by structural modifications. Physical Chemistry Chemical Physics. 2011;13(9):3800-3808.
Siewertsen, R., Strübe, F., Mattay, J., Renth, F., & Temps, F. (2011). Tuning of switching properties and excited-state dynamics of fulgides by structural modifications. Physical Chemistry Chemical Physics, 13(9), 3800-3808. https://doi.org/10.1039/c0cp01890b
Siewertsen, Ron, Strübe, Frank, Mattay, Jochen, Renth, Falk, and Temps, Friedrich. 2011. “Tuning of switching properties and excited-state dynamics of fulgides by structural modifications”. Physical Chemistry Chemical Physics 13 (9): 3800-3808.
Siewertsen, R., Strübe, F., Mattay, J., Renth, F., and Temps, F. (2011). Tuning of switching properties and excited-state dynamics of fulgides by structural modifications. Physical Chemistry Chemical Physics 13, 3800-3808.
Siewertsen, R., et al., 2011. Tuning of switching properties and excited-state dynamics of fulgides by structural modifications. Physical Chemistry Chemical Physics, 13(9), p 3800-3808.
R. Siewertsen, et al., “Tuning of switching properties and excited-state dynamics of fulgides by structural modifications”, Physical Chemistry Chemical Physics, vol. 13, 2011, pp. 3800-3808.
Siewertsen, R., Strübe, F., Mattay, J., Renth, F., Temps, F.: Tuning of switching properties and excited-state dynamics of fulgides by structural modifications. Physical Chemistry Chemical Physics. 13, 3800-3808 (2011).
Siewertsen, Ron, Strübe, Frank, Mattay, Jochen, Renth, Falk, and Temps, Friedrich. “Tuning of switching properties and excited-state dynamics of fulgides by structural modifications”. Physical Chemistry Chemical Physics 13.9 (2011): 3800-3808.

8 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Ultrafast dynamics of the ESIPT photoswitch N-(3-pyridinyl)-2-pyridinecarboxamide.
Böhnke H, Bahrenburg J, Ma X, Röttger K, Näther C, Rode MF, Sobolewski AL, Temps F., Phys Chem Chem Phys 20(4), 2018
PMID: 29319075
First-Principles Prediction of Wavelength-Dependent Product Quantum Yields.
Thompson T, Tapavicza E., J Phys Chem Lett 9(16), 2018
PMID: 30048134
Tuning the photoreactivity of Z-hexatriene photoswitches by substituents - a non-adiabatic molecular dynamics study.
Tapavicza E, Thompson T, Redd K, Kim D., Phys Chem Chem Phys 20(38), 2018
PMID: 30229769
Ultrafast polyene dynamics: the ring opening of 1,3-cyclohexadiene derivatives.
Arruda BC, Sension RJ., Phys Chem Chem Phys 16(10), 2014
PMID: 24457943
Ultrafast Z → E photoisomerisation of structurally modified furylfulgides.
Renth F, Siewertsen R, Strübe F, Mattay J, Temps F., Phys Chem Chem Phys 16(36), 2014
PMID: 25105666
Photochemical dynamics of E-iPr-furylfulgide.
Schönborn JB, Koslowski A, Thiel W, Hartke B., Phys Chem Chem Phys 14(35), 2012
PMID: 22850439
Electronic and steric effects on the photo-induced C→E ring-opening of structurally modified furylfulgides.
Siewertsen R, Strübe F, Mattay J, Renth F, Temps F., Phys Chem Chem Phys 13(34), 2011
PMID: 21799957

62 References

Daten bereitgestellt von Europe PubMed Central.


Heller, J. Chem. Soc., Perkin Trans. 1 (), 1981

Darcy, J. Chem. Soc., Perkin Trans. 1 (), 1981
Fulgides for Memories and Switches.
Yokoyama Y., Chem. Rev. 100(5), 2000
PMID: 11777417
Nonvolatile read-out molecular memory.
Liang YC, Dvornikov AS, Rentzepis PM., Proc. Natl. Acad. Sci. U.S.A. 100(14), 2003
PMID: 12829801
Two-photon three-dimensional optical storage memory.
Dvornikov AS, Walker EP, Rentzepis PM., J Phys Chem A 113(49), 2009
PMID: 19856937

Willner, Angew. Chem., Int. Ed. Engl. 35(), 1996

Willner, Acc. Chem. Res. 30(), 1997

Janicki, J. Am. Chem. Soc. 117(), 1995
Electron and energy transfer modulation with photochromic switches.
Raymo FM, Tomasulo M., Chem Soc Rev 34(4), 2005
PMID: 15778766

Cusido, Eur. J. Org. Chem. (), 2009

Yokoyama, Bull. Chem. Soc. Jpn. 69(), 1996

Yokoyama, J. Chem. Soc., Chem. Commun. (), 1995

Kiji, Bull. Chem. Soc. Jpn. 68(), 1995

Yokoyama, Chem. Lett. (), 1988

Yokoyama, Chem. Lett. (), 1994

Liang, J. Mater. Chem. 10(), 2000
Tuning the optical properties of fluorinated indolylfulgimides.
Wolak MA, Thomas CJ, Gillespie NB, Birge RR, Lees WJ., J. Org. Chem. 68(2), 2003
PMID: 12530855

Yokoyama, Chem. Lett. 20(), 1991

Tomoda, Bull. Chem. Soc. Jpn. 66(), 1993

Yokoyama, Chem. Lett. (), 1996

Handschuh, J. Phys. Chem. A 101(), 1997

Renth, Chem. Phys. Lett. 428(), 2006

Ishibashi, J. Phys. Chem. C 111(), 2007
Accelerated and efficient photochemistry from higher excited electronic states in fulgide molecules.
Cordes T, Malkmus S, DiGirolamo JA, Lees WJ, Nenov A, de Vivie-Riedle R, Braun M, Zinth W., J Phys Chem A 112(51), 2008
PMID: 19049317
Ring-opening reaction of a trifluorinated indolylfulgide: mode-specific photochemistry after pre-excitation.
Draxler S, Brust T, Malkmus S, DiGirolamo JA, Lees WJ, Zinth W, Braun M., Phys Chem Chem Phys 11(25), 2009
PMID: 19562131

Ishibashi, New J. Chem. 33(), 2009

Brust, J. Photochem. Photobiol., A 207(), 2009
Increasing the efficiency of the ring-opening reaction of photochromic indolylfulgides by optical pre-excitation.
Brust T, Draxler S, Eicher J, Lees WJ, Ruck-Braun K, Zinth W, Braun M., Chem Phys Lett 489(4-6), 2010
PMID: 20514344
Stability and reaction dynamics of trifluorinated indolylfulgides.
Brust T, Draxler S, Popp A, Chen X, Lees WJ, Zinth W, Braun M., Chem Phys Lett 477(4-6), 2009
PMID: 20454528
Wavelength and solvent independent photochemistry: the electrocyclic ring-closure of indolylfulgides.
Cordes T, Herzog TT, Malkmus S, Draxler S, Brust T, Digirolamo JA, Lees WJ, Braun M., Photochem. Photobiol. Sci. 8(4), 2009
PMID: 19337667

Port, Mol. Cryst. Liq. Cryst. 430(), 2005

Voll, J. Photochem. Photobiol., A 190(), 2007

Tomasello, Angew. Chem., Int. Ed. 49(), 2010

Uhlmann, J. Photochem. Photobiol., A 98(), 1996

Fuß, Mol. Phys. 104(), 2006

Jacobs, Adv. Photochem. 11(), 1979
Comparing a photoinduced pericyclic ring opening and closure: differences in the excited state pathways.
Heinz B, Malkmus S, Laimgruber S, Dietrich S, Schulz C, Ruck-Braun K, Braun M, Zinth W, Gilch P., J. Am. Chem. Soc. 129(27), 2007
PMID: 17567132

Draxler, J. Mol. Liq. 141(), 2008

Takeuchi, Chem. Phys. Lett. 326(), 2000

Hou, Chem. Phys. Lett. 381(), 2003
Coherent ultrafast torsional motion and isomerization of a biomimetic dipolar photoswitch.
Briand J, Bram O, Rehault J, Leonard J, Cannizzo A, Chergui M, Zanirato V, Olivucci M, Helbing J, Haacke S., Phys Chem Chem Phys 12(13), 2010
PMID: 20237707

Wurzer, Chem. Phys. Lett. 299(), 1999

Kumar, J. Chem. Phys. 114(), 2001
Isomerization through conical intersections.
Levine BG, Martinez TJ., Annu Rev Phys Chem 58(), 2007
PMID: 17291184
Direct observation of the femtosecond excited-state cis-trans isomerization in bacteriorhodopsin.
Mathies RA, Brito Cruz CH, Pollard WT, Shank CV., Science 240(4853), 1988
PMID: 3363359

Fuß, Chem. Phys. 232(), 1998
Bridged photochromic diarylethenes investigated by ultrafast absorption spectroscopy: evidence for two distinct photocyclization pathways.
Aloise S, Sliwa M, Pawlowska Z, Rehault J, Dubois J, Poizat O, Buntinx G, Perrier A, Maurel F, Yamaguchi S, Takeshita M., J. Am. Chem. Soc. 132(21), 2010
PMID: 20455540

Celani, J. Phys. Chem. 100(), 1996

Garavelli, J. Phys. Chem. A 101(), 1997

Hofmann, J. Chem. Phys. 112(), 2000
Cyclohexadiene ring opening observed with 13 fs resolution: coherent oscillations confirm the reaction path.
Kosma K, Trushin SA, Fuss W, Schmid WE., Phys Chem Chem Phys 11(1), 2008
PMID: 19081921
Ultrafast ring-closure reaction of photochromic indolylfulgimides studied with UV-pump-IR-probe spectroscopy.
Koller FO, Schreier WJ, Schrader TE, Malkmus S, Schulz C, Dietrich S, Ruck-Braun K, Braun M., J Phys Chem A 112(2), 2007
PMID: 18095661

Woodward, Angew. Chem., Int. Ed. Engl. 8(), 1969
Highly efficient reversible Z-E photoisomerization of a bridged azobenzene with visible light through resolved S(1)(n pi*) absorption bands.
Siewertsen R, Neumann H, Buchheim-Stehn B, Herges R, Nather C, Renth F, Temps F., J. Am. Chem. Soc. 131(43), 2009
PMID: 19827776

Böckmann, Angew. Chem., Int. Ed. 49(), 2010
Unusual photochemical dynamics of a bridged azobenzene derivative.
Carstensen O, Sielk J, Schonborn JB, Granucci G, Hartke B., J Chem Phys 133(12), 2010
PMID: 20886930
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 21210030
PubMed | Europe PMC

Suchen in

Google Scholar