Efficient blue light emitting materials based on : M -carborane-anthracene dyads. Structure, photophysics and bioimaging studies
Chaari, Mahdi (Institut de Ciència de Materials de Barcelona)
Kelemen, Zsolt (Institut de Ciència de Materials de Barcelona)
Choquesillo-Lazarte, Duane (Laboratorio de Estudios Cristalográficos)
Gaztelumendi, Nerea (Universitat Autònoma de Barcelona. Departament de Biologia Cel·lular, de Fisiologia i d'Immunologia)
Teixidor, Francesc (Institut de Ciència de Materials de Barcelona)
Viñas, Clara (Institut de Ciència de Materials de Barcelona)
Nogués, C. (Carme) (Universitat Autònoma de Barcelona. Departament de Biologia Cel·lular, de Fisiologia i d'Immunologia)
Núñez, Rosario (Institut de Ciència de Materials de Barcelona)

Data:	2019
Resum:	Efficient monosubstitution of the non-iodinated, mono-iodinated and di-iodinated m-carborane cluster at one C has led to the preparation of three single organic molecule-carborane dyads (4-6), which exhibited exceptional fluorescence properties with quantum yield values of 100% in solution, for all of them, with maxima around 415 nm, which correspond to the locally excited state (LE) emission. These results suggest that simply linking the m-carborane fragment to one anthracene unit through a CH spacer produces a significant enhancement of the fluorescence in the final fluorophore, probably due to the free rotation of the anthracene linked to the C. Besides, the presence of one or two iodine atoms linked to boron atoms does not cause any influence on the photophysical properties of the dyads, as it is confirmed by TD-DFT calculations. Notably, the three conjugates show good fluorescence efficiency in the aggregate state with quantum yields in the range of 19-23%, which could be ascribed to the presence of CH, particularly for 4, and the iodine atoms in 5 and 6, which prevent π-π stacking. All these results indicate that our dyads are extremely good emitters in solution while maintaining the emission properties in the aggregate state. Crystal packing, fingerprint plot analysis, and TD-DFT calculations for the three compounds support these results. Confocal microscopy studies show that 6 is the best-internalized compound by HeLa cells via endocytosis, although 4 and 5 also presented a high fluorescence intensity emission. Moreover, due to the blue emission, this compound is an excellent candidate to be applied as a fluorescent dye in bioimaging studies.
Ajuts:	Agència de Gestió d'Ajuts Universitaris i de Recerca 2017/SGR/1720 Agència de Gestió d'Ajuts Universitaris i de Recerca 2017/SGR/503 European Commission MSCA-IF-751587 Ministerio de Economía y Competitividad SEV-2015-0496 Ministerio de Economía y Competitividad CTQ2016-75150-R Ministerio de Economía y Competitividad MAT2017-86357-C3-3-R
Drets:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, la comunicació pública de l'obra i la creació d'obres derivades, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original.
Llengua:	Anglès
Document:	Article ; recerca ; Versió publicada
Matèria:	Blue light emitting materials ; Emission properties ; Fluorescence efficiency ; Fluorescence intensities ; Fluorescence properties ; Locally excited state ; Photophysical properties ; Td-dft calculations ; Anthracenes ; Boranes ; Crystallography ; X-Ray ; Density Functional Theory ; Endocytosis ; Fluorescent Dyes ; HeLa Cells ; Humans ; Microscopy ; Confocal ; Molecular Structure
Publicat a:	Biomaterials science, Vol. 7, Issue 12 (October 2019) , p. 5324-5337, ISSN 2047-4849

DOI: 10.1039/c9bm00903e
PMID: 31620701

14 p, 4.7 MB

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