Remarkable Stability of High Energy Conformers in Self-Assembled Monolayers of a Bistable Electro- and Photoswitchable Overcrowded Alkene

Ivashenko, Oleksii; Logtenberg, Hella; Areephong, Jetsuda; Coleman, Anthony C.; Wesenhagen, Philana V.; Geertsema, Edzard M.; Heureux, Nicolas; Feringa, Ben L.; Rudolf, Petra; Browne, Wesley R.

doi:10.1021/jp206889y

Cited by 45 publications

(51 citation statements)

References 53 publications

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“…[14,15] Upon reduction,t he double bond is restored through step 3( Scheme 3), yieldingb oth the stable (A)a nd unstable( C)c onformations, with the latter undergoing thermal helix inversion to yield A again (step 4, Scheme 3). An overview of the variousp rocesses is presented in the scheme.…”

Section: Discussionmentioning

confidence: 99%

Towards Redox‐Driven Unidirectional Molecular Motion

et al. 2016

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Redox-driven molecular motion is an attractive alternative to light-driven processes. Here, the ability of an overcrowded alkene-based unimolecular light-driven rotary motor (A) to be driven by oxidation/reduction cycles is explored. We show that two-electron oxidation of A is followed by irreversible deprotonation and reduction to form a monocationic species D(+) , in which the stereogenic center is lost. This latter species was isolated through preparative electrolysis and its structure was confirmed by using single-crystal X-ray analysis. However, at short timescales and in the absence of Brønsted acids, these processes can be outrun and the oxidation of A to a dicationic species B(2+) occurs, in which the central double bond (the axle of the molecular motor) becomes a single bond; when followed by rapid reduction, it results in the reformation of A, potentially in both its stable and unstable conformations. The latter conformation, if formed, undergoes thermal helix inversion, completing a rotary cycle. The data obtained regarding these reactions provide a window of opportunity for the motor to be driven electrochemically, without degradation from chemical reactions of the oxidized motor.

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Section: Discussionmentioning

confidence: 99%

Towards Redox‐Driven Unidirectional Molecular Motion

et al. 2016

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“…By the same reasoning, group theory predicts feasible enantiomerizations or inversions if conformations with any two of the three point groups D 2 , C 2h ( y), and C 2v (x) are 228 P.U. Biedermann and I. Agranat accessible to the molecule, i.e., if a molecule can adopt a twisted and an anti-folded conformation, or a twisted and a syn-folded conformation, or an anti-folded and a syn-folded conformation.…”

Section: The Molecular Symmetry Group Of Homomerous Baesmentioning

confidence: 94%

“…30). However, in general, the obtained blends resulted in PV devices exhibiting low energy conversion efficiencies [228].…”

Section: Fullerenes For Organic Photovoltaicsmentioning

confidence: 99%

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Polyarenes II

2014

Topics in Current Chemistry

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“…The most well known of these involve the use of redox active catenanes, [5][6][7][8] metal coordination compounds, [9][10][11][12][13][14][15] rotaxanes, [11,12,14,[16][17][18][19][20][21][22] π-systems, [23][24][25][26][27][28] and crowded alkenes [29]. These systems are finding increasing application in solid-state electronic devices.…”

Section: Open Accessmentioning

confidence: 99%

Redox-Dependent Conformational Switching of Diphenylacetylenes

et al. 2014

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Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1 H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch.

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Remarkable Stability of High Energy Conformers in Self-Assembled Monolayers of a Bistable Electro- and Photoswitchable Overcrowded Alkene

Abstract: Supporting Information. Details of synthesis and characterization, FTIR, Raman, and XPS spectra, electrochemistry, and procedures for preparation of substrates. This material is available free of charge via the Internet at http://pubs.acs.org.

Cited by 45 publications

References 53 publications

Towards Redox‐Driven Unidirectional Molecular Motion

Towards Redox‐Driven Unidirectional Molecular Motion

Polyarenes II

Redox-Dependent Conformational Switching of Diphenylacetylenes

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