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Photochromic Torsional Switch (PTS): a light-driven actuator for the dynamic tuning of π-conjugation extension† †Electronic supplementary information (ESI) available: Synthetic procedures, NMR spectra, TDDFT calculations and excited states assignments. See DOI: 10.1039/c6sc03196j Click here for additional data file.

Authors: Maciejewski, Jan; Sobczuk, Adam; Claveau, Alexis; Nicolai, Adrien; Petraglia, Riccardo; Cervini, Luca; Baudat, Emilie; +4 Authors

Photochromic Torsional Switch (PTS): a light-driven actuator for the dynamic tuning of π-conjugation extension† †Electronic supplementary information (ESI) available: Synthetic procedures, NMR spectra, TDDFT calculations and excited states assignments. See DOI: 10.1039/c6sc03196j Click here for additional data file.

Abstract

Here we present a molecular architecture that can reversibly change the geometric conformation of its π-system backbone via irradiation with two different wavelengths. The proposed ‘molecular actuator’ consists of a photoswitchable azobenzene orthogonally connected to a π-conjugated bithiophene by both direct and aliphatic linker-assisted bonding. Upon exposure to 350 nm light, the trans azobenzene moiety isomerizes to its cis form, causing the bithiophene to assume a semiplanar anti conformation (extended π-conjugation). Exposure to 254 nm light promotes the isomerization of the azobenzene unit back to its initial extended trans conformation, thus forcing the bithiophene fragment to twist out of coplanarity (restricted π-conjugation). The molecular conformation of the bithiophene was characterized using steady-state UV-vis and nuclear magnetic resonance spectroscopy, as well as ab initio computations. The proposed molecular design could be envisaged as a π-conjugation modulator, which has potential to be incorporated into extended linear π-systems, i.e. via the terminal α-thiophene positions, and used to tune their optical and electronic properties.

The conjugation of a bithiophene was reversibly modulated over several cycles through the isomerization of an azobenzene.

Keywords

Chemistry

37 references, page 1 of 4

Conclusions 14 J. Collin, C. Dietrich-Buchecker, P. Gavin˜a, M. C. JimenezMolero and J. Sauvage, Acc. Chem. Res., 2001, 34, 477-487.

In conclusion, a novel molecular actuator capable of modu- 15 G. S. Kottas, L. I. Clarke, D. Horinek and J. Michl, Chem. Rev., lating the extension of its p-conjugated backbone in response to 2005, 105, 1281-1376.

light has been designed. The mechanical motion associated 16 T. R. Kelly, H. De Silva and R. A. Silva, Nature, 1999, 401, 150- with the trans-cis isomerization of an azobenzene has been 152.

translated to a change in the planarity of the connected 17 N. Koumura, R. W. J. Zijlstra, R. A. van Delden, N. Harada bithiophene, thus allowing for the dynamic tuning of its and B. L. Feringa, Nature, 1999, 401, 150-155.

p-conjugation. This work provides a basis for the development 18 T. V. Khuong, H. Dang, P. D. Jarowski, E. F. Maverick and of novel light-driven molecular actuators that can be used to M. A. Garcia-Garibay, J. Am. Chem. Soc., 2007, 129, 839-845.

tune the physical properties of extended p-conjugated system. 19 R. Eelkema, M. M. Pollard, J. Vicario, N. Katsonis, The possibility to integrate the proposed PTS structure into B. S. Ramon, C. W. M. Bastiaansen, D. J. Broer and conjugated oligomers and polymers, i.e. via the terminal B. L. Feringa, Nature, 2006, 440, 163.

a-thiophene positions, can potentially lead to the next-genera- 20 T. Muraoka, K. Kinbara, Y. Kobayashi and T. Aida, J. Am.

tion of photochromic molecular materials with both photo- Chem. Soc., 2003, 125, 5612-5613.

chromic and photoconductive behaviour, and allow for the 21 T. Muraoka, K. Kinbara, Y. Kobayashi and T. Aida, Nature, fabrication of novel light responsive optoelectronic devices. 2006, 440, 512-515.

22 T. Kudernac, N. Ruangsupapichat, M. Parschau, B. Maci`a, Acknowledgements N. NaKatsonis, S. R. Harutyunyan, K. Ernst and B. L. Feringa, Nature, 2011, 479, 208-211.

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    4
    popularity
    This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
    Average
    influence
    This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
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    impulse
    This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
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citations
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
4
Average
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Average
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