Controlling azobenzene photoswitching through combined ortho-fluorination and -amination

被引:62
作者
Ahmed, Z. [1 ]
Siiskonen, A. [1 ]
Virkki, M. [1 ]
Priimagi, A. [1 ]
机构
[1] Tampere Univ Technol, Lab Chem & Bioengn, POB 541, FI-33101 Tampere, Finland
基金
欧洲研究理事会;
关键词
TO-CRYSTAL ISOMERIZATION; VISIBLE-LIGHT; ORTHO-FLUOROAZOBENZENES; PHOTOPHARMACOLOGY; SWITCHES;
D O I
10.1039/c7cc07308a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We present a series of visible-light-absorbing azobenzene photo-switches with cis-lifetimes ranging from one second to three days. We combine ortho-fluorination to control the cis-lifetimes, and ortho-amination to boost the visible-light absorption. The synthesis is accomplished by selectively replacing one or more ortho-fluorines with amines in the ortho-fluoroazobenzene precursors.
引用
收藏
页码:12520 / 12523
页数:4
相关论文
共 35 条
[1]   ACTIVATING INFLUENCE OF PARA-GROUPS ON THE LABILITY OF CHLORINE IN CHLOROBENZENES [J].
BADGER, GM ;
COOK, JW ;
VIDAL, WP .
JOURNAL OF THE CHEMICAL SOCIETY, 1947, (AUG) :1109-1109
[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]   Visible-Light-Activated Molecular Switches [J].
Bleger, David ;
Hecht, Stefan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (39) :11338-11349
[6]   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
[7]   A Roadmap to Success in Photopharmacology [J].
Broichhagen, Johannes ;
Frank, James Allen ;
Trauner, Dirk .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (07) :1947-1960
[8]   Shape-Shifting Azo Dye Polymers: Towards Sunlight-Driven Molecular Devices [J].
Bushuyev, Oleksandr S. ;
Aizawa, Miho ;
Shishido, Atsushi ;
Barrett, Christopher J. .
MACROMOLECULAR RAPID COMMUNICATIONS, 2018, 39 (01)
[9]   Photo-mechanical azobenzene cocrystals and in situ X-ray diffraction monitoring of their optically-induced crystal-to-crystal isomerisation [J].
Bushuyev, Oleksandr S. ;
Corkery, T. Christopher ;
Barrett, Christopher J. ;
Friscic, Tomislav .
CHEMICAL SCIENCE, 2014, 5 (08) :3158-3164
[10]   Shaping Crystals with Light: Crystal-to-Crystal Isomerization and Photomechanical Effect in Fluorinated Azobenzenes [J].
Bushuyev, Oleksandr S. ;
Tomberg, Anna ;
Friscic, Tomislav ;
Barrett, Christopher J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (34) :12556-12559