Diversity-oriented synthesis of blue emissive nitrogen heterocycles and their conjugation with carbon nano-onions

doi:10.1007/s11705-019-1833-0

Front. Chem. Sci. Eng.

2020, Vol. 14

Issue (1) : 76-89 https://doi.org/10.1007/s11705-019-1833-0

RESEARCH ARTICLE

Diversity-oriented synthesis of blue emissive nitrogen heterocycles and their conjugation with carbon nano-onions

Viviana Maffeis¹, Lisa Moni², Daniele Di Stefano², Silvia Giordani^1,³(

), Renata Riva⁴(

)

¹. Nano Carbon Materials, Istituto Italiano di Tecnologia (IIT), 10144 Torino, Italy
². Department of Chemistry and Industrial Chemistry, University of Genova, 16146 Genova, Italy
³. School of Chemical Sciences, Dublin City University,?Dublin 9,?Ireland
⁴. Department of Pharmacy, University of Genova, 16147 Genova, Italy

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Abstract

The search for new fluorescent molecules for possible applications as functional p-electron systems and their conjugation with different nanomaterials is nowadays of paramount importance to broaden the availability of materials with different properties. Herein we present a diversity-oriented approach to heterocyclic luminophores based on a multicomponent Ugi reaction followed by a Pd-mediated cascade sequence. The new molecules are coupled to carbon nano-onions, and hybrid systems represent the first example of blue emitters conjugated with these carbon nanoparticles.

Keywords carbon nano-onions multicomponent reactions blue emitters fluorescence isoquinolines

Corresponding Author(s): Silvia Giordani,Renata Riva

Just Accepted Date: 29 April 2019 Online First Date: 26 June 2019 Issue Date: 20 January 2020

Cite this article:

Viviana Maffeis,Lisa Moni,Daniele Di Stefano, et al. Diversity-oriented synthesis of blue emissive nitrogen heterocycles and their conjugation with carbon nano-onions[J]. Front. Chem. Sci. Eng., 2020, 14(1): 76-89.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-019-1833-0
https://academic.hep.com.cn/fcse/EN/Y2020/V14/I1/76

Fig.1 Scheme 1 Synthetic strategy to furo[2,3-c]isoquinolines 2

Fig.2 Scheme 2 Synthesis of furo[2,3-c]isoquinolines 21–23

Fig.3 Scheme 3 Ligation of fluorophores 21–23 to ox-CNOs

Fig.4 (a) TGA analysis of CNOs before (ox-CNO) and after ligation (1-CNO, 2-CNO, 3-CNO), and (b) absorption and (c) emission spectra of fluorophores (21, 22 and 23) before and after ligation.

Fig.5 Effective hydrodynamic diameter obtained from DLS measurements of 1-CNO, 2-CNO and 3-CNO

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