Diversity-oriented synthesis of blue emissive nitrogen heterocycles and their conjugation with carbon nano-onions
Viviana Maffeis1, Lisa Moni2, Daniele Di Stefano2, Silvia Giordani1,3(), 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
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.
. [J]. Frontiers of Chemical Science and Engineering, 2020, 14(1): 76-89.
Viviana Maffeis, Lisa Moni, Daniele Di Stefano, Silvia Giordani, Renata Riva. Diversity-oriented synthesis of blue emissive nitrogen heterocycles and their conjugation with carbon nano-onions. Front. Chem. Sci. Eng., 2020, 14(1): 76-89.
O Mykhailiv, H Zubyk, M E Plonska-Brzezinska. Carbon nano-onions: Unique carbon nanostructures with fascinating properties and their potential applications. Inorganica Chimica Acta, 2017, 468: 49–66 https://doi.org/10.1016/j.ica.2017.07.021
5
A Palkar, F Melin, C M Cardona, B Elliott, A K Naskar, D D Edie, A Kumbhar, L Echegoyen. Reactivity differences between carbon nano onions (cnos) prepared by different methods. Chemistry, an Asian Journal, 2007, 2(5): 625–633 https://doi.org/10.1002/asia.200600426
6
V L Kuznetsov, I L Zilberberg, Y V Butenko, A L Chuvilin, B Segall. Theoretical study of the formation of closed curved graphite-like structures during annealing of diamond surface. Journal of Applied Physics, 1999, 86(2): 863–870 https://doi.org/10.1063/1.370816
7
N Sano, H Wang, I Alexandrou, M Chhowalla, K B K Teo, G A J Amaratunga, K Iimura. Properties of carbon onions produced by an arc discharge in water. Journal of Applied Physics, 2002, 92(5): 2783–2788 https://doi.org/10.1063/1.1498884
8
I Alexandrou, H Wang, N Sano, G A J Amaratunga. Structure of carbon onions and nanotubes formed by arc in liquids. Journal of Chemical Physics, 2004, 120(2): 1055–1058 https://doi.org/10.1063/1.1629274
9
D Dorobantu, P M Bota, I Boerasu, D Bojin, M Enachescu. Pulse laser ablation system for carbon nano-onions fabrication. Surface Engineering and Applied Electrochemistry, 2014, 50(5): 390–394 https://doi.org/10.3103/S1068375514050044
10
X H Chen, F M Deng, J X Wang, H S Yang, G T Wu, X B Zhang, J C Peng, W Z Li. New method of carbon onion growth by radio-frequency plasma-enhanced chemical vapor deposition. Chemical Physics Letters, 2001, 336(3): 201–204 https://doi.org/10.1016/S0009-2614(01)00085-9
11
J Bartelmess, S Giordani. Carbon nano-onions (multi-layer fullerenes): Chemistry and applications. Beilstein Journal of Nanotechnology, 2014, 5: 1980–1998 https://doi.org/10.3762/bjnano.5.207
12
V Georgakilas, D M Guldi, R Signorini, R Bozio, M Prato. Organic functionalization and optical properties of carbon onions. Journal of the American Chemical Society, 2003, 125(47): 14268–14269 https://doi.org/10.1021/ja0342805
13
Y Liu, R L Vander Wal, V N Khabashesku. Functionalization of carbon nano-onions by direct fluorination. Chemistry of Materials, 2007, 19(4): 778–786 https://doi.org/10.1021/cm062177j
14
A S Rettenbacher, M W Perpall, L Echegoyen, J Hudson, D W Smith. Radical addition of a conjugated polymer to multilayer fullerenes (carbon nano-onions). Chemistry of Materials, 2007, 19(6): 1411–1417 https://doi.org/10.1021/cm0626132
15
C T Cioffi, A Palkar, F Melin, A Kumbhar, L Echegoyen, M Melle-Franco, F Zerbetto, G M A Rahman, C Ehli, V Sgobba, D M Guldi, M Prato. A carbon nano-onion–ferrocene donor–acceptor system: Synthesis, characterization and properties. Chemistry (Weinheim an der Bergstrasse, Germany), 2009, 15(17): 4419–4427 https://doi.org/10.1002/chem.200801818
16
L Zhou, C Gao, D Zhu, W Xu, F F Chen, A Palkar, L Echegoyen, E S W Kong. Facile functionalization of multilayer fullerenes (carbon nano-onions) by nitrene chemistry and “grafting from” strategy. Chemistry (Weinheim an der Bergstrasse, Germany), 2009, 15(6): 1389–1396 https://doi.org/10.1002/chem.200801642
17
K Flavin, M N Chaur, L Echegoyen, S Giordani. Functionalization of multilayer fullerenes (carbon nano-onions) using diazonium compounds and “click” chemistry. Organic Letters, 2010, 12(4): 840–843 https://doi.org/10.1021/ol902939f
18
S Tomita, M Fujii, S Hayashi, K Yamamoto. Electron energy-loss spectroscopy of carbon onions. Chemical Physics Letters, 1999, 305(3): 225–229 https://doi.org/10.1016/S0009-2614(99)00374-7
19
M Chhowalla, H Wang, N Sano, K B K Teo, S B Lee, G A J Amaratunga. Carbon onions: Carriers of the 217.5 nm interstellar absorption feature. Physical Review Letters, 2003, 90(15): 155504 https://doi.org/10.1103/PhysRevLett.90.155504
20
S Sek, J Breczko, M E Plonska-Brzezinska, A Z Wilczewska, L Echegoyen. STM-based molecular junction of carbon nano-onion. ChemPhysChem, 2013, 14(1): 96–100 https://doi.org/10.1002/cphc.201200624
21
M Zeiger, N Jäckel, M Aslan, D Weingarth, V Presser. Understanding structure and porosity of nanodiamond-derived carbon onions. Carbon, 2015, 84: 584–598 https://doi.org/10.1016/j.carbon.2014.12.050
22
O Shenderova, T Tyler, G Cunningham, M Ray, J Walsh, M Casulli, S Hens, G McGuire, V Kuznetsov, S Lipa. Nanodiamond and onion-like carbon polymer nanocomposites. Diamond and Related Materials, 2007, 16(4): 1213–1217 https://doi.org/10.1016/j.diamond.2006.11.086
23
J Macutkevic, R Adomavicius, A Krotkus, D Seliuta, G Valusis, S Maksimenko, P Kuzhir, K Batrakov, V Kuznetsov, S Moseenkov, O Shenderova, A V Okotrub, R Langlet, P Lambin. Terahertz probing of onion-like carbon-PMMA composite films. Diamond and Related Materials, 2008, 17(7): 1608–1612 https://doi.org/10.1016/j.diamond.2007.11.018
24
J P Bartolome, L Echegoyen, A Fragoso. Reactive carbon nano-onion modified glassy carbon surfaces as DNA sensors for human papillomavirus oncogene detection with enhanced sensitivity. Analytical Chemistry, 2015, 87(13): 6744–6751 https://doi.org/10.1021/acs.analchem.5b00924
25
V Maffeis, R O McCourt, R Petracca, O Laethem, A Camisasca, P E Colavita, S Giordani, E M Scanlan. Photocatalytic initiation of radical thiol-ene reactions using carbon-B2O3 nanocomposites. ACS Applied Nano Materials, 2018, 1(8): 4120–4126 https://doi.org/10.1021/acsanm.8b00870
26
M Zeiger, N Jäckel, V N Mochalin, V Presser. Review: Carbon onions for electrochemical energy storage. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2016, 4(9): 3172–3196 https://doi.org/10.1039/C5TA08295A
27
D Zheng, G Yang, Y Zheng, P Fan, R Ji, J Huang, W Zhang, J Yu. Carbon nano-onions as a functional dopant to modify hole transporting layers for improving stability and performance of planar perovskite solar cells. Electrochimica Acta, 2017, 247: 548–557 https://doi.org/10.1016/j.electacta.2017.07.061
28
M D’Amora, M Rodio, J Bartelmess, G Sancataldo, R Brescia, F Cella Zanacchi, A Diaspro, S Giordani. Biocompatibility and biodistribution of functionalized carbon nano-onions (f-CNOs) in a vertebrate model. Scientific Reports, 2016, 6(1): 33923 https://doi.org/10.1038/srep33923
29
M D’Amora, A Camisasca, S Lettieri, S Giordani. Toxicity assessment of carbon nanomaterials in zebrafish during development. Nanomaterials (Basel, Switzerland), 2017, 7(12): 414 https://doi.org/10.3390/nano7120414
30
M Trusel, M Baldrighi, R Marotta, F Gatto, M Pesce, M Frasconi, T Catelani, F Papaleo, P P Pompa, R Tonini, S Giordani. Internalization of carbon nano-onions by hippocampal cells preserves neuronal circuit function and recognition memory. ACS Applied Materials & Interfaces, 2018, 10(20): 16952–16963 https://doi.org/10.1021/acsami.7b17827
31
S Lettieri, M d’Amora, A Camisasca, A Diaspro, S Giordani. Carbon nano-onions as fluorescent on/off modulated nanoprobes for diagnostics. Beilstein Journal of Nanotechnology, 2017, 8: 1878–1888 https://doi.org/10.3762/bjnano.8.188
32
T J J Müller, U H F Bunz. Functional Organic Materials. Syntheses, Strategies, and Applications. Weinheim: Wiley-VCH, 2007
33
F Arcudi, L Đorđević, M Prato. Rationally designed carbon nanodots towards pure white-light rmission. Angewandte Chemie International Edition, 2017, 56(15): 4170–4173 https://doi.org/10.1002/anie.201612160
34
M Frasconi, R Marotta, L Markey, K Flavin, V Spampinato, G Ceccone, L Echegoyen, E M Scanlan, S Giordani. Multi-functionalized carbon nano-onions as imaging probes for cancer cells. Chemistry (Weinheim an der Bergstrasse, Germany), 2015, 21(52): 19071–19080 https://doi.org/10.1002/chem.201503166
35
J Bartelmess, M Baldrighi, V Nardone, E Parisini, D Buck, L Echegoyen, S Giordani. Synthesis and characterization of far-red/NIR-fluorescent BODIPY dyes, solid-state fluorescence, and application as fluorescent tags attached to carbon nano-onions. Chemistry (Weinheim an der Bergstrasse, Germany), 2015, 21(27): 9727–9732 https://doi.org/10.1002/chem.201500877
36
S Lettieri, A Camisasca, M d’Amora, A Diaspro, T Uchida, Y Nakajima, K Yanagisawa, T Maekawa, S Giordani. Far-red fluorescent carbon nano-onions as a biocompatible platform for cellular imaging. RSC Advances, 2017, 7(72): 45676–45681 https://doi.org/10.1039/C7RA09442F
37
Y Liu, D Y Kim. Ultraviolet and blue emitting graphene quantum dots synthesized from carbon nano-onions and their comparison for metal ion sensing. Chemical Communications, 2015, 51(20): 4176–4179 https://doi.org/10.1039/C4CC07618D
38
K Müllen, U Scherf. Organic light-emitting diodes—synthesis, properties, and applications. Weinheim: Wiley-VCH, 2006
39
M Zhu, C Yang. Blue fluorescent emitters: Design tactics and applications in organic light-emitting diodes. Chemical Society Reviews, 2013, 42(12): 4963–4976 https://doi.org/10.1039/c3cs35440g
40
H Kuma, C Hosokawa. Blue fluorescent OLED materials and their application for high-performance devices. Science and Technology of Advanced Materials, 2014, 15(3): 34201 https://doi.org/10.1088/1468-6996/15/3/034201
41
X Yang, X Xu, G Zhou. Recent advances of the emitters for high performance deep-blue organic light-emitting diodes. Journal of Materials Chemistry. C, Materials for Optical and Electronic Devices, 2015, 3(5): 913–944 https://doi.org/10.1039/C4TC02474E
42
T T Bui, F Goubard, M Ibrahim-Ouali, D Gigmes, F Dumur. Thermally activated delayed fluorescence emitters for deep blue organic light emitting diodes: A review of recent advances. Applied Sciences (Basel, Switzerland), 2018, 8(4): 494 https://doi.org/10.3390/app8040494
43
J D Froehlich, R Young, T Nakamura, Y Ohmori, S Li, A Mochizuki, M Lauters, G E Jabbour. Synthesis of Multi-Functional POSS Emitters for OLED Applications. Chemistry of Materials, 2007, 19(20): 4991–4997 https://doi.org/10.1021/cm070726v
44
F Krujatz, O R Hild, K Fehse, M Jahnel, A Werner, T Bley. Exploiting the potential of oled-based photo-organic sensors for biotechnological applications. Chemical Sciences Journal, 2016, 7(3): 134
45
C W Cairo, J A Key, C M Sadek. Fluorescent small-molecule probes of biochemistry at the plasma membrane. Current Opinion in Chemical Biology, 2010, 14(1): 57–63 https://doi.org/10.1016/j.cbpa.2009.09.032
46
Y Hong, M Häußler, J W Y Lam, Z Li, K K Sin, Y Dong, H Tong, J Liu, A Qin, R Renneberg, B Z Tang. Label-free fluorescent probing of G-quadruplex formation and real-time monitoring of dna folding by a quaternized tetraphenylethene salt with aggregation-induced emission characteristics. Chemistry (Weinheim an der Bergstrasse, Germany), 2008, 14(21): 6428–6437 https://doi.org/10.1002/chem.200701723
47
V L Kuznetsov, A L Chuvilin, Y V Butenko, I Y Mal’kov, V M Titov. Onion-like carbon from ultra-disperse diamond. Chemical Physics Letters, 1994, 222(4): 343–348 https://doi.org/10.1016/0009-2614(94)87072-1
48
M Frasconi, V Maffeis, J Bartelmess, S Giordani. Highly surface functionalized carbon nano-onions for bright light bioimaging. Methods and Applications in Fluorescence, 2015, 3(4): 0044005 https://doi.org/10.1088/2050-6120/3/4/044005
49
L Moni, C F Gers-Panther, M Anselmo, T J J Müller, R Riva. Highly convergent synthesis of intensively blue emissive furo[2,3-c]isoquinolines by a palladium-catalyzed cyclization cascade of unsaturated Ugi products. Chemistry (Weinheim an der Bergstrasse, Germany), 2016, 22(6): 2020–2031 https://doi.org/10.1002/chem.201504335
50
A Dömling. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chemical Reviews, 2006, 106(1): 17–89 https://doi.org/10.1021/cr0505728
51
R Hu, N L C Leung, B Z Tang. AIE macromolecules: Syntheses, structures and functionalities. Chemical Society Reviews, 2014, 43(13): 4494–4562 https://doi.org/10.1039/C4CS00044G
52
L Banfi, A Basso, L Giardini, R Riva, V Rocca, G Guanti. Tandem Ugi MCR/Mitsunobu cyclization as a short, protecting-group-free route to benzoxazinones with four diversity points. European Journal of Organic Chemistry, 2010, 2011(1): 100–109 https://doi.org/10.1002/ejoc.201001077
53
B Söveges, T Imre, Á L Póti, P Sok, Z Kele, A Alexa, P Kele, K Németh. Tracking down protein–protein interactions via a FRET-system using site-specific thiol-labeling. Organic & Biomolecular Chemistry, 2018, 16(32): 5756–5763 https://doi.org/10.1039/C8OB00742J
54
J Bartelmess, E De Luca, A Signorelli, M Baldrighi, M Becce, R Brescia, V Nardone, E Parisini, L Echegoyen, P P Pompa, et al. Boron dipyrromethene (BODIPY) functionalized carbon nano-onions for high resolution cellular imaging. Nanoscale, 2014, 6(22): 13761–13769 https://doi.org/10.1039/C4NR04533E
55
S Giordani, J Bartelmess, M Frasconi, I Biondi, S Cheung, M Grossi, D Wu, L Echegoyen, D F O’Shea. NIR fluorescence labelled carbon nano-onions: Synthesis, analysis and cellular imaging. Journal of Materials Chemistry. B, Materials for Biology and Medicine, 2014, 2(42): 7459–7463 https://doi.org/10.1039/C4TB01087F
