A facile approach to the preparation of bis-crown ethers based on SET-promoted photomacrocyclization reactions.
A novel methodology for the synthesis of bis-crown ethers has been developed. The preparative route takes advantage of an efficient single electron transfer promoted photomacrocyclization reaction of polyether branched bisphthalimides which contain alpha-trimethylsilylmethyl groups at terminal positions. The generality of the methodology was demonstrated by its application to the synthesis of symmetric and unsymmetric bis-crown ethers of various ring sizes. Finally, the metal cation binding and fluorescence emission properties of the bis-crowns, prepared by using the developed procedure, were briefly explored.
Sung
Nam Kyung
NK
Department of Chemistry, College of Natural Sciences, Pusan National University, Busan, Korea.
Cho
Dae Won
DW
Choi
Jung Hei
JH
Choi
Kyung Wha
KW
Yoon
Ung Chan
UC
Maeda
Hajime
H
Mariano
Patrick S
PS
D043844:Crown Ethers / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D003500:Cyclization; D004583:Electrons; D008027:Light; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D008670:Metals / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects; D010777:Photochemistry; D010797:Phthalimides / Q000737:chemistry; D013237:Stereoisomerism
D043844:Crown Ethers; D047028:Macrocyclic Compounds; D008670:Metals; D009942:Organometallic Compounds; D010797:Phthalimides