PUBLICATION
Two-Photon Absorbing AIEgens: Influence of Stereoconfiguration on Their Crystallinity and Spectroscopic Properties and Applications in Bioimaging
- Authors
- Rouillon, J., Blahut, J., Jean, M., Albalat, M., Vanthuyne, N., Lesage, A., Ali, L.M.A., Hadj-Kaddour, K., Onofre, M., Gary-Bobo, M., Micouin, G., Banyasz, A., Le Bahers, T., Andraud, C., Monnereau, C.
- ID
- ZDB-PUB-201121-10
- Date
- 2020
- Source
- ACS applied materials & interfaces 12(49): 55157-55168 (Journal)
- Registered Authors
- Keywords
- aggregation-induced emission, bioimaging, crystallinity, stereoconfiguration, two-photon absorption
- MeSH Terms
-
- Aniline Compounds/chemistry*
- Animals
- Breast Neoplasms/metabolism
- Breast Neoplasms/pathology
- Contrast Media/chemistry*
- Embryo, Nonmammalian/anatomy & histology
- Female
- Fluorescent Dyes/chemistry
- Humans
- Isomerism
- MCF-7 Cells
- Microscopy, Fluorescence, Multiphoton
- Nanoparticles/chemistry
- Optical Imaging/methods*
- Stilbenes/chemistry*
- Zebrafish/growth & development
- PubMed
- 33217234 Full text @ ACS Appl. Mater. Interfaces
Citation
Rouillon, J., Blahut, J., Jean, M., Albalat, M., Vanthuyne, N., Lesage, A., Ali, L.M.A., Hadj-Kaddour, K., Onofre, M., Gary-Bobo, M., Micouin, G., Banyasz, A., Le Bahers, T., Andraud, C., Monnereau, C. (2020) Two-Photon Absorbing AIEgens: Influence of Stereoconfiguration on Their Crystallinity and Spectroscopic Properties and Applications in Bioimaging. ACS applied materials & interfaces. 12(49):55157-55168.
Abstract
This paper aims at designing chromophores with efficient aggregation-induced emission (AIE) properties for two-photon fluorescence microscopy (2PFM), which is one of the best-suited types of microscopy for the imaging of living organisms or thick biological tissues. Tetraphenylethylene (TPE) derivatives are common building blocks in the design of chromophores with efficient AIE properties. Therefore, in this study, extended TPE AIEgens specifically optimized for two-photon absorption (2PA) are synthesized and the resulting (E/Z) isomers are separated using chromatography on chiral supports. Comparative characterization of the AIE properties is performed on the pure (Z) and (E) isomers and the mixture, allowing us, in combination with powder X-ray diffraction and solid-state NMR, to document a profound impact of crystallinity on solid-state fluorescence properties. In particular, we show that stereopure AIEgens form aggregates of superior crystallinity, which in turn exhibit a higher fluorescence quantum yield compared to diastereoisomers mixtures. Preparation of stereopure organic nanoparticles affords very bright fluorescent contrast agents, which are then used for cellular and intravital two-photon microscopy on human breast cancer cells and on zebrafish embryos.
Genes / Markers
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Orthology
Engineered Foreign Genes
Mapping