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
Einrichtung
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.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
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
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
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
Tapavicza E, Thompson T, Redd K, Kim D., Phys Chem Chem Phys 20(38), 2018
PMID: 30229769
Photochemical dynamics of E-methylfurylfulgide-kinematic effects on photorelaxation dynamics of furylfulgides.
Schönborn JB, Hartke B., Phys Chem Chem Phys 16(6), 2014
PMID: 24358466
Schönborn JB, Hartke B., Phys Chem Chem Phys 16(6), 2014
PMID: 24358466
Ultrafast polyene dynamics: the ring opening of 1,3-cyclohexadiene derivatives.
Arruda BC, Sension RJ., Phys Chem Chem Phys 16(10), 2014
PMID: 24457943
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
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
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
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
Nonvolatile read-out molecular memory.
Liang YC, Dvornikov AS, Rentzepis PM., Proc. Natl. Acad. Sci. U.S.A. 100(14), 2003
PMID: 12829801
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
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
Raymo FM, Tomasulo M., Chem Soc Rev 34(4), 2005
PMID: 15778766
Cusido, Eur. J. Org. Chem. (), 2009
Linear and Nonlinear Optical Properties of Photochromic Molecules and Materials.
Delaire JA, Nakatani K., Chem. Rev. 100(5), 2000
PMID: 11777422
Delaire JA, Nakatani K., Chem. Rev. 100(5), 2000
PMID: 11777422
Nonlinear optical switching properties in the furylfulgide aberchrome 540-dihydrobenzofuran derivative pair of photochromic materials.
Seal P, Chakrabarti S., J Phys Chem A 114(1), 2010
PMID: 19919075
Seal P, Chakrabarti S., J Phys Chem A 114(1), 2010
PMID: 19919075
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
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
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
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
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
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
Cordes T, Herzog TT, Malkmus S, Draxler S, Brust T, Digirolamo JA, Lees WJ, Braun M., Photochem. Photobiol. Sci. 8(4), 2009
PMID: 19337667
Parallel ultrafast E-C ring closure and E-Z isomerisation in a photochromic furylfulgide studied by femtosecond time-resolved spectroscopy.
Siewertsen R, Renth F, Temps F, Sonnichsen F., Phys Chem Chem Phys 11(28), 2009
PMID: 19588018
Siewertsen R, Renth F, Temps F, Sonnichsen F., Phys Chem Chem Phys 11(28), 2009
PMID: 19588018
Port, Mol. Cryst. Liq. Cryst. 430(), 2005
Voll, J. Photochem. Photobiol., A 190(), 2007
Tomasello, Angew. Chem., Int. Ed. 49(), 2010
Kinetic analysis and elucidation options for AB(1k,2phi) systems. New spectrokinetic methods for photochromes.
Maafi M, Brown RG., Photochem. Photobiol. Sci. 7(11), 2008
PMID: 18958323
Maafi M, Brown RG., Photochem. Photobiol. Sci. 7(11), 2008
PMID: 18958323
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
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
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
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
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
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
Kosma K, Trushin SA, Fuss W, Schmid WE., Phys Chem Chem Phys 11(1), 2008
PMID: 19081921
Beyond the van der Lugt/Oosterhoff model: when the conical intersection seam and the S1 minimum energy path do not cross.
Nenov A, Kolle P, Robb MA, de Vivie-Riedle R., J. Org. Chem. 75(1), 2010
PMID: 19954144
Nenov A, Kolle P, Robb MA, de Vivie-Riedle R., J. Org. Chem. 75(1), 2010
PMID: 19954144
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
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
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
Carstensen O, Sielk J, Schonborn JB, Granucci G, Hartke B., J Chem Phys 133(12), 2010
PMID: 20886930
Superior Z→E and E→Z photoswitching dynamics of dihydrodibenzodiazocine, a bridged azobenzene, by S1(nπ*) excitation at λ = 387 and 490 nm.
Siewertsen R, Schonborn JB, Hartke B, Renth F, Temps F., Phys Chem Chem Phys 13(3), 2010
PMID: 21072405
Siewertsen R, Schonborn JB, Hartke B, Renth F, Temps F., Phys Chem Chem Phys 13(3), 2010
PMID: 21072405
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 21210030
PubMed | Europe PMC
Suchen in