Boron difluoride complexes of 2'-hydroxychalcones and curcuminoids as fluorescent dyes for photonic applications

Tóm tắt

The field of fluorescent boron complexes has witnessed tremendous developments in recent years. In that context, we have investigated two series of boron difluoride complexes based on 2'-hydroxychalcone and curcuminoid ligands that represent naturally occurring pigment structures. The dyes display significantly large Stokes shift values, indicating that an ICT state is involved as lower-energy state in the singlet manifold. Remarkably they are also fluorescent in the solid-state, with emission wavelengths usually in the visible and mainly in the near infrared (NIR). It is especially intriguing that those dyes experience strong π-interactions in the crystal phase. We have observed that the formation of those highly stacked structures was not detrimental to solid-state emission and could even be exploited for the generation of efficient NIR emitters. For example, the boron complexes of curcuminoid ligands can be used to generate NIR fluorescent organic nanoparticles with large cross sections for two-photon absorption. The design of organic dyes displaying NIR emission in solution or in the solid-state remains challenging for applications in bioimaging and organic photonics.

Từ khoá

curcuminoids, boron complexes, solid-state fluorescence, near infrared, organic nanoparticles

Tài liệu tham khảo

Shimizu M and Hiyama T 2010 Chem. Asian J. 5 1516
Hong Y, Lama J W Y and Tang B Z 2009 Chem.Commun. 4332
Massin J, Dayoub W, Mulatier J-C, Aronica C, Bretonnière Y and Andraud C 2011 Chem. Mater. 23 862
Kaeser A and Schenning A P H J 2010 Adv. Mater. 22 2985
Li K et al 2013 Sci. Rep. 3 1150
Robinson M R, Wang S, Heeger A J and Bazan G C 2001 Adv. Funct. Mater. 11 413
Hong Y, Lam J W Y and Tang B Z 2011 Chem. Soc. Rev. 40 5361
An B-K, Gierschner J and Park S Y 2012 Acc. Chem. Res. 45 544
D’Aléo A and Fages F 2014 Display and Imaging 2 149
Rao Y-L and Wang S 2011 Inorg. Chem. 50 12263
Grealis J P, Müller-Bunz H, Ortin Y, Casey M and McGlinchey M J 2013 Eur. J. Org. Chem. 332
Szmant H H and Basso A J 1952 J. Am. Chem. Soc. 74 4397
Szmant H H and Planinsek H J 1954 J. Am. Chem. Soc. 76 1193
Black W B and Lutz R E 1955 J. Am. Chem. Soc. 77 5134
Roque A, Lodeiro C, Pina F, Maestri M, Dumas S, Passaniti P and Balzani V 2003 J. Am. Chem. Soc. 125 987
Ravindra H J, Chandrashekaran K, Harrison W T A and Dharmaprakash S M 2009 Appl. Phys. B 94 503
Ribierre J-C, Mager L, Fort A and Méry S 2003 Macromolecules 36 2516
Kumar S K, Hager E, Pettit C, Gurulingappa H, Davidson N E and Khan S R 2003 J. Med. Chem. 46 2813
Nowakowska Z 2007 Eur. J. Med. Chem. 42 125
Esatbeyoglu T, Huebbe P, Ernst I M A, Chin D, Wagner A E and Rimbach G 2012 Angew. Chem. Int. Ed. 51 5308
D’Aléo A, Gachet D, Heresanu V, Giorgi M and Fages F 2012 Chem.–Eur. J. 18 12764
Felouat A, D’Aléo A and Fages F 2013 J. Org. Chem. 78 4446
Fabian J and Hartmann H 2004 J. Phys. Org. Chem. 17 359
Alemany P, D’Aléo A, Giorgi M, Canadell E and Fages F 2014 Cryst. Growth Des. 14 3700
Rurack K, Bricks J L, Reck G, Radeglia R and Resch-Genger U 2000 J. Phys. Chem. A 104 3087
Van Allan J A and Reynolds G A 1969 J. Heterocycl. Chem. 6 29
Chou P-T, Martinez M L and Cooper W C 1992 J. Am. Chem. Soc. 114 4943
Rajib Ghosh R, Mondal J A and Palit D K 2010 J. Phys. Chem. B 114 12129
Chambon S, D’Aléo A, Baffert C, Wantz G and Fages F 2013 Chem. Commun. 49 3555
Cogné-Laage E, Allemand J-F, Ruel O, Baudin J-B, Croquette V, Blanchard-Desce M and Jullien L 2004 Chem. Eur. J. 10 1445
Gierschner J, Lüer L, Milián-Medina B, Oelkrug D and Egelhaaf H-J 2013 J. Phys. Chem. Lett. 4 2686
D’Aléo A, Heresanu V, Giorgi M, Le Guennic B, Jacquemin D and Fages F 2014 J. Phys. Chem. C 118 11919
D’Aléo A, Felouat A, Heresanu V, Ranguis A, Chaudanson D, Karapetyan A, Giorgi M and Fages F 2014 J. Mater. Chem. C 2 5208
He G S, Tan L-S, Zheng Q and Prasad P N 2008 Chem. Rev. 108 1245
Terenziani F, Katan C, Badaeva E, Tretiak S and Blanchard-Desce M 2008 Adv. Mater. 20 4641
Hales J M, Matichak J, Barlow S, Ohira S, Yesudas K, Brédas J-L, Perry J W and Marder S R 2010 Science 327 1485
Li Z et al 2012 Adv. Mater. 24 OP326
Matsui K, Segawa Y, Namikawa T, Kamada K and Itami K 2013 Chem. Sci. 4 84
Andraud C and Maury O 2009 Eur. J. Inorg. Chem. 4343
Yao S and Belfield K D 2012 Eur. J. Inorg. Chem. 3199
De Meulenaere E et al 2012 Chem. Sci. 3 984
D'Aléo A, Pointillart F, Ouahab L, Andraud C and Maury O 2012 Coord. Chem. Rev. 256 1604
Ftouni H, Bolze F, de Rocquigny H and Nicoud J-F 2013 Bioconjugate Chem. 24 942
Hilderbrand S A and Weissleder R 2010 Curr. Opin. Chem. Biol. 14 71
Yuan A, Wu J, Tang X, Zhao L, Xu F and Hu Y 2013 J. Pharma. Sci. 102 6
Hu H et al 2013 Phys. Chem. Chem. Phys. 15 7666
Padilha L A et al 2010 J. Phys. Chem. A 114 6493
D’Aléo A, Bourdolle A, Brustlein S, Fauquier T, Grichine A, Duperray A, Baldeck P L, Andraud C, Brasselet S and Maury O 2012 Angew. Chem. Int. Ed. 51 6622
Zhang T, Zhu X, Cheng C C W, Kwok W-M, Tam H-L, Hao J, Kwong D W J, Wong W-K and Wong K L 2011 J. Am. Chem. Soc. 133 20120
Garcia-Alloza M, Borrelli L A, Rozkalne A, Hyman B T and Bacskai B J 2007 J. Neurochem. 102 1095
Yanagisawa D, Amatsubo T, Morikawa S, Taguchi H, Urushitani M, Shirai N, Hirao K, Shiino A, Inubushi T and Tooyama I 2011 Neuroscience 184 120
Chittigori J, Kumar A, Li L, Thota S, Kokil A, Samuelson L A, Sandman D J and Kumar J 2014 Tetrahedron 70 991
Kunwar A, Barik A, Mishra B, Rathinasamy K, Pandey R and Priyadarsini K I 2008 BBA-Gen. Subjects 1780 673
Kumar A, Li L, Chaturvedi A, Brzostowski J, Chittigori J, Pierce S, Samuelson L A, Sandman D and Kumar J 2012 Appl. Phys. Lett. 100 203701
Liu K, Chen J, Chojnacki J and Zhang S 2013 Tetrahedron Lett. 54 2070
Ran C, Xu X, Raymond S B, Ferrara B J, Neal K, Bacskai B J, Medarova Z and Moore A 2009 J. Am. Chem. Soc. 131 15257
Zhang X, Tian Y, Li Z, Tian X, Sun H, Liu H, Moore A and Ran C 2013 J. Am. Chem. Soc. 135 16397
McClain W M 1974 Acc. Chem. Res. 7 129
Terenziani F, Painelli A, Katan C, Charlot M and Blanchard-Desce M 2006 J. Am. Chem. Soc. 128 15742
Bellier Q, Makarov N S, Bouit P-A, Rigaut S, Kamada K, Feneyrou P, Berginc G, Maury O, Perry J W and Andraud C 2012 Phys. Chem. Chem. Phys. 14 15299
Kawai H, Nalwa H S, Oikawa H, Okada S, Matsuda H, Minami N, Kakuda A, Ono K, Mukoh A and Nakanishi H 1992 Japan. J. Appl. Phys. 31 L1132
Geng J, Li K, Ding D, Zhang X, Qin W, Liu J, Tang B Z and Liu B 2012 Small 8 3655
Parthasarathy V, Fery-Forgues S, Campioli E, Recher G, Terenziani F and Blanchard-Desce M 2011 Small 7 3219
Ishow E, Brosseau A, Clavier G, Nakatani K, Tauc P, Fiorini-Debuisschert C, Neveu S, Sandre O and Léaustic A 2008 Chem. Mater. 20 6597
Jiang Y, Wang Y, Hua J, Tang J, Li B, Qian S and Tian H 2010 Chem. Commun. 46 4689
Noh S B, Kim R H, Kim W J, Kim S, Lee K-S, Cho N S, Shim H-K, Pudavar H E and Prasad P N 2010 J. Mater. Chem. 20 7422
Massin J, Charaf-Eddin A, Appaix F, Bretonnière Y, Jacquemin D, van der Sanden B, Monnereau C and Andraud C 2013 Chem. Sci. 4 2833

Các bài trích dẫn đến

1. Peng-Zhong Chen, Li-Ya Niu, Yu-Zhe Chen, Qing-Zheng Yang. Difluoroboron β-diketonate dyes: spectroscopic properties and applications in Coordination Chemistry Reviews (Vol. 350, 2017)
2. Pierre‐Henri Lanoë, Bastien Mettra, Yuan Yuan Liao, Nathalie Calin, Anthony D'Aléo, Tomotaka Namikawa, Kenji Kamada, Fréderic Fagès, Cyrille Monnereau, Chantal Andraud. Theoretical and Experimental Study on Boron β‐Diketonate Complexes with Intense Two‐Photon‐Induced Fluorescence in Solution and in the Solid State in ChemPhysChem (Vol. 17, No. 14, 2016)
3. Sven M Elbert, Philippe Wagner, Thines Kanagasundaram, Frank Rominger, Michael Mastalerz. Boroquinol Complexes with Fused Extended Aromatic Backbones: Synthesis and Optical Properties in Chemistry–A European Journal (Vol. 23, No. 4, 2017)
4. Hua Liu, Ji-Huan Yang, Lu Lin, Dun-Jia Wang, Ling Fan, Yan-Jun Hu. Synthesis, characterization, and photoluminescence properties of difluoroboron complexes with bis-β-diketone ligands in Research on Chemical Intermediates (Vol. 42, No. 4, 2016)
5. Miguel Ponce-Vargas, Bogdan Štefane, Elena Zaborova, Frédéric Fages, Anthony D'Aléo, Denis Jacquemin, Boris Le Guennic. Searching for new borondifluoride β-diketonate complexes with enhanced absorption/emission properties using ab initio tools in Dyes and Pigments (Vol. 155, 2018)
6. Cristina Jiménez, Alejandro Enríquez-Cabrera, Oscar González-Antonio, Javier Ordóñez-Hernández, Pascal Lacroix, Pablo Labra-Vázquez, Norberto Farfán, Rosa Santillan. State of the Art of Boron and Tin Complexes in Second-and Third-Order Nonlinear Optics § in Inorganics (Vol. 6, No. 4, 2018)
7. Raymond E Borg, Maryam Hatamimoslehabadi, Stephanie Bellinger, Jeffrey La, Farha Mithila, Chandra Yelleswarapu, Jonathan Rochford. Photophysical and Photoacoustic Properties of π‐Extended Curcumin Dyes. Effects of the Terminal Dimethylamino Electron‐donor and the Bridging Aryl Ring in Photochemistry and photobiology (Vol. 95, No. 1, 2019)
8. Yu Li, Lingyu Zeng, Cheng Zhong, Xiaohu Dong, Zhiqiang Mao, Zhihong Liu, Songwei Lv, Zhengguo Zhang, Jingui Qin. A Two‐Photon Dye with Favorable Photophysical Properties and Ultrahigh Polarity Sensitivity Designed by Utilizing the Tautomerism of β‐Diketone in Advanced Optical Materials (Vol. 5, No. 2, 2017)