On the Computational Design of Azobenzene-Based Multi-State Photoswitches

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2022 Aug 12

PMID 35955820

Authors

Miquel Moreno

Jose M Lluch

Ricard Gelabert

Affiliations

Soon will be listed here.

Abstract

In order to theoretically design multi-state photoswitches with specific properties, an exhaustive computational study is first carried out for an azobenzene dimer that has been recently synthesized and experimentally studied. This study allows for a full comprehension of the factors that govern the photoactivated isomerization processes of these molecules so to provide a conceptual/computational protocol that can be applied to generic multi-state photoswitches. From this knowledge a new dimer with a similar chemical design is designed and also fully characterized. Our theoretical calculations predict that the new dimer proposed is one step further in the quest for a double photoswitch, where the four metastable isomers could be selectively interconverted through the use of different irradiation sequences.

References

Merino E, Ribagorda M . Control over molecular motion using the cis-trans photoisomerization of the azo group. Beilstein J Org Chem. 2012; 8:1071-90. PMC: 3458724. DOI: 10.3762/bjoc.8.119. View

Bahrenburg J, Sievers C, Schonborn J, Hartke B, Renth F, Temps F . Photochemical properties of multi-azobenzene compounds. Photochem Photobiol Sci. 2012; 12(3):511-8. DOI: 10.1039/c2pp25291k. View

Robertus J, Reker S, Pijper T, Deuzeman A, Browne W, Feringa B . Kinetic analysis of the thermal isomerisation pathways in an asymmetric double azobenzene switch. Phys Chem Chem Phys. 2012; 14(13):4374-82. DOI: 10.1039/c2cp23756c. View

Zapata F, Fernandez-Gonzalez M, Rivero D, Alvarez A, Marazzi M, Frutos L . Toward an Optomechanical Control of Photoswitches by Tuning Their Spectroscopical Properties: Structural and Dynamical Insights into Azobenzene. J Chem Theory Comput. 2015; 10(1):312-23. DOI: 10.1021/ct4007629. View

Ankenbruck N, Courtney T, Naro Y, Deiters A . Optochemical Control of Biological Processes in Cells and Animals. Angew Chem Int Ed Engl. 2017; 57(11):2768-2798. PMC: 6026863. DOI: 10.1002/anie.201700171. View

Knie C, Utecht M, Zhao F, Kulla H, Kovalenko S, Brouwer A . ortho-Fluoroazobenzenes: visible light switches with very long-Lived Z isomers. Chemistry. 2014; 20(50):16492-501. DOI: 10.1002/chem.201404649. View

Bleger D, Dokic J, Peters M, Grubert L, Saalfrank P, Hecht S . Electronic decoupling approach to quantitative photoswitching in linear multiazobenzene architectures. J Phys Chem B. 2011; 115(33):9930-40. DOI: 10.1021/jp2044114. View

Corchado J, Sanchez M, Fdez Galvan I, Martin M, Munoz-Losa A, Barata-Morgado R . Theoretical study of solvent effects on the ground and low-lying excited free energy surfaces of a push-pull substituted azobenzene. J Phys Chem B. 2014; 118(43):12518-30. DOI: 10.1021/jp506876v. View

Reuter R, Wegner H . Oligoazobenzenophanes--synthesis, photochemistry and properties. Chem Commun (Camb). 2011; 47(45):12267-76. DOI: 10.1039/c1cc13773e. View

10.

Coskun A, Banaszak M, Astumian R, Stoddart J, Grzybowski B . Great expectations: can artificial molecular machines deliver on their promise?. Chem Soc Rev. 2011; 41(1):19-30. DOI: 10.1039/c1cs15262a. View

11.

Weigend F . Accurate Coulomb-fitting basis sets for H to Rn. Phys Chem Chem Phys. 2006; 8(9):1057-65. DOI: 10.1039/b515623h. View

12.

Klajn R . Spiropyran-based dynamic materials. Chem Soc Rev. 2013; 43(1):148-84. DOI: 10.1039/c3cs60181a. View

13.

Slavov C, Yang C, Schweighauser L, Boumrifak C, Dreuw A, Wegner H . Connectivity matters - ultrafast isomerization dynamics of bisazobenzene photoswitches. Phys Chem Chem Phys. 2016; 18(22):14795-804. DOI: 10.1039/c6cp00603e. View

14.

Heindl A, Becker J, Wegner H . Selective switching of multiple azobenzenes. Chem Sci. 2019; 10(31):7418-7425. PMC: 6713861. DOI: 10.1039/c9sc02347j. View

15.

Manna D, Udayabhaskararao T, Zhao H, Klajn R . Orthogonal light-induced self-assembly of nanoparticles using differently substituted azobenzenes. Angew Chem Int Ed Engl. 2015; 54(42):12394-7. DOI: 10.1002/anie.201502419. View

16.

Galanti A, Santoro J, Mannancherry R, Duez Q, Diez-Cabanes V, Valasek M . A New Class of Rigid Multi(azobenzene) Switches Featuring Electronic Decoupling: Unravelling the Isomerization in Individual Photochromes. J Am Chem Soc. 2019; 141(23):9273-9283. DOI: 10.1021/jacs.9b02544. View

17.

Beharry A, Woolley G . Azobenzene photoswitches for biomolecules. Chem Soc Rev. 2011; 40(8):4422-37. DOI: 10.1039/c1cs15023e. View

18.

Sadovski O, Beharry A, Zhang F, Woolley G . Spectral tuning of azobenzene photoswitches for biological applications. Angew Chem Int Ed Engl. 2009; 48(8):1484-6. DOI: 10.1002/anie.200805013. View

19.

Liang J, Feng X, Hait D, Head-Gordon M . Revisiting the Performance of Time-Dependent Density Functional Theory for Electronic Excitations: Assessment of 43 Popular and Recently Developed Functionals from Rungs One to Four. J Chem Theory Comput. 2022; 18(6):3460-3473. DOI: 10.1021/acs.jctc.2c00160. View

20.

Szymanski W, Beierle J, Kistemaker H, Velema W, Feringa B . Reversible photocontrol of biological systems by the incorporation of molecular photoswitches. Chem Rev. 2013; 113(8):6114-78. DOI: 10.1021/cr300179f. View