Shaping Crystals with Light: Crystal-to-Crystal Isomerization and Photomechanical Effect in Fluorinated Azobenzenes

被引：263
作者：
Bushuyev, Oleksandr S.
Tomberg, Anna
Friscic, Tomislav [1 ]
Barrett, Christopher J.
机构：
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 0B8, Canada
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 34期
基金：
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词：
SINGLE-CRYSTAL; MOTION; PHOTOISOMERIZATION; PHOTOSWITCHES; PHOTODRIVEN; SWITCHES; BEHAVIOR; FILMS;
D O I：
10.1021/ja4063019
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Unusually long thermal half-lives of perhalogenated cis-azobenzenes enabled their structural characterization and the first evidence of a crystal-to-crystal cis -> trans azobenzene isomerization. Irradiation with visible light transforms a perhalogenated cis-azobenzene single crystal into a polycrystalline aggregate of its trans-isomer in a photomechanical transformation that involves a significant, controllable, and thermally irreversible change of crystal shape. This is the first demonstration of permanent photomechanical modification of crystal shape in an azobenzene.
引用
收藏
页码：12556 / 12559
页数：4
相关论文
共 49 条
[1]   Photochemically driven shape changes of crystalline organic nanorods [J].
Al-Kaysi, Rabih O. ;
Mueller, Astrid M. ;
Bardeen, Christopher J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) :15938-15939
[2]   Photoisomerization in different classes of azobenzene [J].
Bandara, H. M. Dhammika ;
Burdette, Shawn C. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (05) :1809-1825
[3]   Azobenzene Photoswitching without Ultraviolet Light [J].
Beharry, Andrew A. ;
Sadovski, Oleg ;
Woolley, G. Andrew .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19684-19687
[4]   Azobenzene photoswitches for biomolecules [J].
Beharry, Andrew A. ;
Woolley, G. Andrew .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (08) :4422-4437
[5]   o-Fluoroazobenzenes as Readily Synthesized Photoswitches Offering Nearly Quantitative Two-Way Isomerization with Visible Light [J].
Bleger, David ;
Schwarz, Jutta ;
Brouwer, Albert M. ;
Hecht, Stefan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (51) :20597-20600
[6]   Fast, Reversible, and General Photomechanical Motion in Single Crystals of Various Azo Compounds Using Visible Light [J].
Bushuyev, Oleksandr S. ;
Singleton, Thomas A. ;
Barrett, Christopher J. .
ADVANCED MATERIALS, 2013, 25 (12) :1796-1800
[7]   Theoretical study of the isomerization mechanism of azobenzene and disubstituted azobenzene derivatives [J].
Crecca, Christina R. ;
Roitberg, Adrian E. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (26) :8188-8203
[8]   Single-crystal-to-single-crystal [2+2] photodimerizations: from discovery to design [J].
Friscic, T ;
MacGillivray, LR .
ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 2005, 220 (04) :351-363
[9]   A theoretical study of the lowest electronic states of azobenzene: the role of torsion coordinate in the cis-trans photoisomerization [J].
Gagliardi, L ;
Orlandi, G ;
Bernardi, F ;
Cembran, A ;
Garavelli, M .
THEORETICAL CHEMISTRY ACCOUNTS, 2004, 111 (2-6) :363-372
[10]   Optical switches for remote and noninvasive control of cell signaling [J].
Gorostiza, Pau ;
Isacoff, Ehud Y. .
SCIENCE, 2008, 322 (5900) :395-399
12345