Deliberate Switching of Single Photochromic Triads

Overview

Journal Sci Rep

Specialty Science

Date 2017 Feb 1

PMID 28139764

Authors

Johannes Maier

Martti Pars

Tina Weller

Mukundan Thelakkat

Jurgen Kohler

Affiliations

Soon will be listed here.

Abstract

Photochromic molecules can be reversibly converted between two bistable conformations by light, and are considered as promising building blocks in novel macromolecular structures for sensing and imaging techniques. We have studied individual molecular triads consisting of two strong fluorophores (perylene bisimide) that are covalently linked via a photochromic unit (dithienylcyclopentene) and distinguished between deliberate switching and spontaneous blinking. It was verified that the probability for observing deliberate light-induced switching of a single triad (rather than stochastic blinking) amounts to 0.8 ± 0.1. In a few exceptional cases this probability can exceed 0.95. These numbers are sufficiently large for application in sensitive biosensing, and super-resolution imaging. This opens the possibility to develop devices that can be controlled by an external optical stimulus on a truly molecular length scale.

References

Nevskyi O, Sysoiev D, Oppermann A, Huhn T, Woll D . Nanoscopic Visualization of Soft Matter Using Fluorescent Diarylethene Photoswitches. Angew Chem Int Ed Engl. 2016; 55(41):12698-702. DOI: 10.1002/anie.201606791. View

Fukaminato T, Doi T, Tamaoki N, Okuno K, Ishibashi Y, Miyasaka H . Single-molecule fluorescence photoswitching of a diarylethene-perylenebisimide dyad: non-destructive fluorescence readout. J Am Chem Soc. 2011; 133(13):4984-90. DOI: 10.1021/ja110686t. View

Toyama T, Higashiguchi K, Nakamura T, Yamaguchi H, Kusaka E, Matsuda K . Photoswitching of Conductance of Diarylethene-Gold Nanoparticle Network Based on the Alteration of π-Conjugation. J Phys Chem Lett. 2016; 7(11):2113-8. DOI: 10.1021/acs.jpclett.6b00993. View

Fukaminato T, Tanaka M, Doi T, Tamaoki N, Katayama T, Mallick A . Fluorescence photoswitching of a diarylethene-perylenebisimide dyad based on intramolecular electron transfer. Photochem Photobiol Sci. 2010; 9(2):181-7. DOI: 10.1039/b9pp00131j. View

van de Linde S, Sauer M . How to switch a fluorophore: from undesired blinking to controlled photoswitching. Chem Soc Rev. 2013; 43(4):1076-87. DOI: 10.1039/c3cs60195a. View

Betzig E . Single Molecules, Cells, and Super-Resolution Optics (Nobel Lecture). Angew Chem Int Ed Engl. 2015; 54(28):8034-53. DOI: 10.1002/anie.201501003. View

El Gemayel M, Borjesson K, Herder M, Duong D, Hutchison J, Ruzie C . Optically switchable transistors by simple incorporation of photochromic systems into small-molecule semiconducting matrices. Nat Commun. 2015; 6:6330. DOI: 10.1038/ncomms7330. View

Orgiu E, Crivillers N, Herder M, Grubert L, Patzel M, Frisch J . Optically switchable transistor via energy-level phototuning in a bicomponent organic semiconductor. Nat Chem. 2012; 4(8):675-9. DOI: 10.1038/nchem.1384. View

Bossi M, Belov V, Polyakova S, Hell S . Reversible red fluorescent molecular switches. Angew Chem Int Ed Engl. 2006; 45(44):7462-5. DOI: 10.1002/anie.200602591. View

10.

Yokoyama Y . Fulgides for Memories and Switches. Chem Rev. 2002; 100(5):1717-1740. DOI: 10.1021/cr980070c. View

11.

Fukaminato T, Sasaki T, Kawai T, Tamai N, Irie M . Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level. J Am Chem Soc. 2004; 126(45):14843-9. DOI: 10.1021/ja047169n. View

12.

Weil T, Vosch T, Hofkens J, Peneva K, Mullen K . The rylene colorant family--tailored nanoemitters for photonics research and applications. Angew Chem Int Ed Engl. 2010; 49(48):9068-93. DOI: 10.1002/anie.200902532. View

13.

Irie M . Diarylethenes for Memories and Switches. Chem Rev. 2002; 100(5):1685-1716. DOI: 10.1021/cr980069d. View

14.

Su J, Fukaminato T, Placial J, Onodera T, Suzuki R, Oikawa H . Giant Amplification of Photoswitching by a Few Photons in Fluorescent Photochromic Organic Nanoparticles. Angew Chem Int Ed Engl. 2016; 55(11):3662-6. DOI: 10.1002/anie.201510600. View

15.

Browne W, Feringa B . Light switching of molecules on surfaces. Annu Rev Phys Chem. 2008; 60:407-28. DOI: 10.1146/annurev.physchem.040808.090423. View

16.

Moerner W . Single-Molecule Spectroscopy, Imaging, and Photocontrol: Foundations for Super-Resolution Microscopy (Nobel Lecture). Angew Chem Int Ed Engl. 2015; 54(28):8067-93. DOI: 10.1002/anie.201501949. View

17.

Brust T, Draxler S, Eicher J, Lees W, Ruck-Braun K, Zinth W . Increasing the efficiency of the ring-opening reaction of photochromic indolylfulgides by optical pre-excitation. Chem Phys Lett. 2010; 489(4-6):175-180. PMC: 2877210. DOI: 10.1016/j.cplett.2010.02.071. View

18.

Pars M, Gradmann M, Graf K, Bauer P, Thelakkat M, Kohler J . Optical gating with organic building blocks. A quantitative model for the fluorescence modulation of photochromic perylene bisimide dithienylcyclopentene triads. Sci Rep. 2014; 4:4316. PMC: 3949285. DOI: 10.1038/srep04316. View

19.

Lippitz M, Kulzer F, Orrit M . Statistical evaluation of single nano-object fluorescence. Chemphyschem. 2005; 6(5):770-89. DOI: 10.1002/cphc.200400560. View

20.

Pars M, Hofmann C, Willinger K, Bauer P, Thelakkat M, Kohler J . An organic optical transistor operated under ambient conditions. Angew Chem Int Ed Engl. 2011; 50(48):11405-8. DOI: 10.1002/anie.201104193. View