[4+4] Photodimerization of Anthracene Derivatives: Recent Synthetic Advances and Applications

被引:16
作者
Liu, Weigang [1 ,2 ]
Guo, Lifeng [1 ,2 ]
Fan, Yangyang [1 ,2 ]
Huang, Zeao [1 ,2 ]
Cong, Huan [1 ,2 ]
机构
[1] Chmese Acad Sci, Tech Inst Phys & Chem, CAS Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
[2] Chinese Acad Sci, Sch Future Technol, Beijing 100190, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
anthmcene; photochemistry; dimenzation; 4+4] cycloadthrion; synthetic applications; ENANTIODIFFERENTIATING PHOTOCYCLODIMERIZATION; SUPRAMOLECULAR PHOTOCHIROGENESIS; GAMMA-CYCLODEXTRIN; INTRAMOLECULAR PHOTOCYCLOADDITION; PHOTOCHEMICAL-REACTIONS; ULTIMATE STEREOCONTROL; 2-DIMENSIONAL POLYMER; SERUM ALBUMINS; STATE; REGIOSELECTIVITY;
D O I
10.6023/cjoc20161101
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The [4+4] photodimerizations of anthracene and its derivatives have been extensively studied for over a century. This classic photochemical reaction features broad substrate scope, user-friendly operation, and controllable reversibility. However, the synthetic applications of anthracene photodimerizations have been underdeveloped thus far, largely because of stereoisomer separation and solubility problems of the dianthracene products. Considering that the dianthracene products display unique molecular rigidity and geometry, further studies to improve the synthetic utility of anthracene photodimerizations should be warranted. This review summarizes the representative works of anthracene photodimerizations since the beginning of the 21st century, highlighting the synthetic. advances to improve the reaction regio- and enanto-selectivity, as well as the synthetic applications toward functional organic molecules and molecular machines.
引用
收藏
页码:543 / 554
页数:12
相关论文
共 65 条
[1]   Engineering atomic and molecular nanostructures at surfaces [J].
Barth, JV ;
Costantini, G ;
Kern, K .
NATURE, 2005, 437 (7059) :671-679
[2]   UNIMOLECULAR PHOTOCHEMISTRY OF ANTHRACENES [J].
BECKER, HD .
CHEMICAL REVIEWS, 1993, 93 (01) :145-172
[3]   Double diels-alder strategies to soluble 2,9- and 2,9,6,13-tetraethynylpentacenes, photolytic [4+4] cycloadditions, and pentacene crystal packing [J].
Benard, Christophe P. ;
Geng, Zhe ;
Heuft, Matthew A. ;
VanCrey, Kelly ;
Fallis, Alex G. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7229-7236
[4]   Photodimerization of anthracenes in fluid solution: structural aspects [J].
Bouas-Laurent, H ;
Castellan, A ;
Desvergne, JP ;
Lapouyade, R .
CHEMICAL SOCIETY REVIEWS, 2000, 29 (01) :43-55
[5]   Photodimerization of anthracenes in fluid solutions: (part 2) mechanistic aspects of the photocycloaddition and of the photochemical and thermal cleavage [J].
Bouas-Laurent, H ;
Castellan, A ;
Desvergne, JP ;
Lapouyade, R .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :248-263
[6]  
Cao DR, 2001, ANGEW CHEM INT EDIT, V40, P186, DOI 10.1002/1521-3773(20010105)40:1<186::AID-ANIE186>3.0.CO
[7]  
2-X
[8]   Photoswitching of the antiferromagnetic coupling in an oxamato-based dicopper(II) anthracenophane [J].
Castellano, Maria ;
Ferrando-Soria, Jesus ;
Pardo, Emilio ;
Julve, Miguel ;
Lloret, Francesc ;
Mathoniere, Corine ;
Pasan, Jorge ;
Ruiz-Perez, Catalina ;
Canadillas-Delgado, Laura ;
Ruiz-Garcia, Rafael ;
Cano, Joan .
CHEMICAL COMMUNICATIONS, 2011, 47 (39) :11035-11037
[9]  
Chih-Kai L., 2013, CHEM-EUR J, V19, P12748
[10]   Excited-State Dynamics Achieved Ultimate Stereocontrol of Photocyclodimerization of Anthracenecarboxylates on a Glucose Scaffold [J].
Fukuhara, Gaku ;
Iida, Kazuhiro ;
Kawanami, Yuko ;
Tanaka, Hidekazu ;
Mori, Tadashi ;
Inoue, Yoshihisa .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (47) :15007-15014