Photoinduced Pedalo-Type Motion in an Azodicarboxamide-Based Molecular Switch

被引：20

作者：

Amirjalayer, Saeed ^{[1
,2
,3
]}

Martinez-Cuezva, Alberto ^{[4
]}

Berna, Jose ^{[4
]}

Woutersen, Sander ^{[5
]}

Buma, Wybren Jan ^{[5
]}

机构：

[1] Westfal Wilhelms Univ Munster, Phys Inst, Willhelm Klemm Str 10, D-48149 Munster, Germany

[2] Westfal Wilhelms Univ Munster, Ctr Multiscale Theory & Computat, Willhelm Klemm Str 10, D-48149 Munster, Germany

[3] Ctr Nanotechnol CeNTech, Heisenbergstr 11, D-48149 Munster, Germany

[4] Univ Murcia, Fac Quim, Dept Quim Organ, E-30100 Murcia, Spain

[5] Univ Amsterdam, Vant Hoff Inst Mol Sci, Sci Pk 904, NL-1098 XH Amsterdam, Netherlands

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 07期

关键词：

density functional theory; molecular switches; photochemistry; photochromism; time-resolved infrared spectroscopy; INFRARED-SPECTROSCOPY; AMPHIDYNAMIC CRYSTALS; DRUG-DELIVERY; REAL-TIME; MACHINES; LIGHT; AZOBENZENE; PHOTOISOMERIZATION; CHEMISTRY; STIMULI;

D O I：

10.1002/anie.201709666

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Well-defined structural changes of molecular units that can be triggered by light are crucial for the development of photoactive functional materials. Herein, we report on a novel switch that has azodicarboxamide as its photo-triggerable element. Time-resolved UV-pump/IR probe spectroscopy in combination with quantum-chemical calculations shows that the azodicarboxamide functionality, in contrast to other azo-based chromophores, does not undergo trans-cis photoisomerization. Instead, a photoinduced pedalo-type motion occurs, which because of its volume-conserving properties enables the design of functional molecular systems with controllable motion in a confined space.

引用

页码：1792 / 1796

页数：5

共 67 条

[1] Controlling Motion at the Nanoscale: Rise of the Molecular Machines [J].

Abendroth, John M. ;

Bushuyev, Oleksandr S. ;

Weiss, Paul S. ;

Barrett, Christopher J. .

ACS NANO, 2015, 9 (08) :7746-7768

[2] Multistate Photo-Induced Relaxation and Photoisomerization Ability of Fumaramide Threads: A Computational and Experimental Study [J].

Altoe, Piero ;

Haraszkiewicz, Natalia ;

Gatti, Francesco G. ;

Wiering, Piet G. ;

Frochot, Celine ;

Brouwer, Albert M. ;

Balkowski, Grzegorz ;

Shaw, Daniel ;

Woutersen, Sander ;

Buma, Wybren Jan ;

Zerbetto, Francesco ;

Orlandi, Giorgio ;

Leigh, David A. ;

Garavelli, Marco .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (01) :104-117

[3] Direct Observation of a Dark State in the Photocycle of a Light-Driven Molecular Motor [J].

Amirjalayer, Saeed ;

Cnossen, Arjen ;

Browne, Wesley R. ;

Feringa, Ben L. ;

Buma, Wybren J. ;

Woutersen, Sander .

JOURNAL OF PHYSICAL CHEMISTRY A, 2016, 120 (43) :8606-8612

[4]

[Anonymous], 2013, ANGEW CHEM, V125, P13067

[5]

[Anonymous], 2015, ANGEW CHE

[6]

[Anonymous], ANGEW CHEM

[7] Evolution of molecular machines: from solution to soft matter interface [J].

Ariga, Katsuhiko ;

Mori, Taizo ;

Hill, Jonathan P. .

SOFT MATTER, 2012, 8 (01) :15-20

[8] How molecular motors work - insights from the molecular machinist's toolbox: the Nobel prize in Chemistry 2016 [J].

Astumian, R. D. .

CHEMICAL SCIENCE, 2017, 8 (02) :840-845

[9] Redox divergent conversion of a [2]rotaxane into two distinct degenerate partners with different shuttling dynamics [J].

Berna, Jose ;

Alajarin, Mateo ;

Marin-Rodriguez, Catalina ;

Franco-Pujante, Carlos .

CHEMICAL SCIENCE, 2012, 3 (07) :2314-2320

[10] Azodicarboxamides as Template Binding Motifs for the Building of Hydrogen-Bonded Molecular Shuttles [J].

Berna, Jose ;

Alajarin, Mateo ;

Orenes, Raul-Angel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) :10741-10747

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