Donor−Acceptor−Donor Fluorene Derivatives for Two-Photon Fluorescence Lysosomal Imaging
摘要:
As part of a strategy to achieve large two-photon absorptivity in fluorene-based probes, a series of donor- acceptor-donor (D-A-D) type derivatives were synthesized and their two-photon absorption (2PA) properties investigated. The synthesis of D-A-D fluorophores was achieved by efficient preparation of key intermediates for the introduction of central electron acceptor groups. To accomplish the synthesis of two of the new derivatives, a high-yield method for a one-step direct dibromomethylation of phenyl sulfide was developed. The linear and nonlinear optical properties, including UV-vis absorption, fluorescence emission, fluorescence anisotropy, and two-photon absorption (2PA), of the new D-A-D compounds were measured and compared to their D-A or D-D counterparts. Fully conjugated acceptor moieties in the center of the D-A-D fluorophore led to the greatest increase in the 2PA cross section, while weakly conjugated central acceptors exhibited only a modest increase in the 2PA cross section relative to D-A diploar analogs. Encapsulation of the new probes in Pluronic F 108N F micelles, and subsequent incubation in HCT 116 cells, resulted in very high lysosomal colocalization (> 0.98 colocalization coefficient) relative to commercial Lysotracker Red, making the micelle-encapsulated dyes particularly attractive as fluorescent probes for two-photon fluorescence microscopy lysosomal imaging.
Donor−Acceptor−Donor Fluorene Derivatives for Two-Photon Fluorescence Lysosomal Imaging
摘要:
As part of a strategy to achieve large two-photon absorptivity in fluorene-based probes, a series of donor- acceptor-donor (D-A-D) type derivatives were synthesized and their two-photon absorption (2PA) properties investigated. The synthesis of D-A-D fluorophores was achieved by efficient preparation of key intermediates for the introduction of central electron acceptor groups. To accomplish the synthesis of two of the new derivatives, a high-yield method for a one-step direct dibromomethylation of phenyl sulfide was developed. The linear and nonlinear optical properties, including UV-vis absorption, fluorescence emission, fluorescence anisotropy, and two-photon absorption (2PA), of the new D-A-D compounds were measured and compared to their D-A or D-D counterparts. Fully conjugated acceptor moieties in the center of the D-A-D fluorophore led to the greatest increase in the 2PA cross section, while weakly conjugated central acceptors exhibited only a modest increase in the 2PA cross section relative to D-A diploar analogs. Encapsulation of the new probes in Pluronic F 108N F micelles, and subsequent incubation in HCT 116 cells, resulted in very high lysosomal colocalization (> 0.98 colocalization coefficient) relative to commercial Lysotracker Red, making the micelle-encapsulated dyes particularly attractive as fluorescent probes for two-photon fluorescence microscopy lysosomal imaging.
Counter-rotatable dual cinchona quinuclidinium salts and their phase transfer catalysis in enantioselective alkylation of glycine imines
作者:Jiin Oh、Jihyeon Park、Keepyung Nahm
DOI:10.1039/d1cc02785a
日期:——
Dual cinchona quinuclidinium salts with a diphenyl ether linker were synthesized and used as powerful asymmetric phasetransfer catalysts in the α-alkylation of imines of glycine and alanine ester with 0.01–0.1 mol% loading (17 examples, 92–99% ee). Skewed conformers of dual quinuclidiniums at TS were proposed to rationalize their high efficiency via DFT calculations.
NOVEL SULFUR COMPOUNDS AND PROCESS FOR PRODUCING THE SAME
申请人:SUMITOMO SEIKA CHEMICALS CO., LTD.
公开号:EP0791579A1
公开(公告)日:1997-08-27
A novel sulfur-containing compound represented by the general formula (I):
wherein n is an integer from 0 to 2; R represents a hydrogen atom, a vinyl group, a methacryloyl group, a vinylbenzyl group, a glycidyl group, an acryloyl group or an allyl group; and the case where n is 0 and R is a hydrogen atom is excluded, and a method for preparing said sulfur-containing compound. The novel sulfur-containing compound of the present invention can be copolymerized with various copolymerizable compounds to yield excellent hardened products of high refractive index. The novel sulfur-containing compound of the present invention can therefore be used as a very useful monomer for the production of optical materials, paints, adhesives, sealants, etc. having excellent properties.
一种通式(I)代表的新型含硫化合物:
其中 n 为 0 至 2 的整数;R 代表氢原子、乙烯基、甲基丙烯酰基、乙烯基苄基、缩水甘油基、丙烯酰基或烯丙基;不包括 n 为 0 和 R 为氢原子的情况,以及制备所述含硫化合物的方法。本发明的新型含硫化合物可与各种可共聚化合物共聚,从而得到高折射率的优良硬化产品。因此,本发明的新型含硫化合物可作为一种非常有用的单体,用于生产具有优异性能的光学材料、涂料、粘合剂、密封剂等。