Aqueous Photon Upconversion by Anionic Acceptors Self-Assembled on Cationic Bilayer Membranes with a Long Triplet Lifetime

Deepak Asthana; Shota Hisamitsu; Masa-aki Morikawa; Pengfei Duan; Takuya Nakashima; Tsuyoshi Kawai; Nobuhiro Yanai; Nobuo Kimizuka

doi:10.1055/s-0039-3400250

CC BY-NC-ND 4.0 · Organic Materials 2019; 01(01): 043-049
DOI: 10.1055/s-0039-3400250

Short Communication

The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2019) The Author(s).

Aqueous Photon Upconversion by Anionic Acceptors Self-Assembled on Cationic Bilayer Membranes with a Long Triplet Lifetime

Authors

Deepak Asthana

^aDepartment of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan

^bSchool of Chemistry, The University of Manchester, Manchester, United Kingdom
Shota Hisamitsu

^aDepartment of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
Masa-aki Morikawa

^aDepartment of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
Pengfei Duan

^aDepartment of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan

^cNational Center for Nanoscience and Technology, Zhongguancun, Beijing, China
Takuya Nakashima

^dGraduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Nara, Japan
Tsuyoshi Kawai

^dGraduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Nara, Japan
Nobuhiro Yanai

^aDepartment of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan

^ePRESTO, JST, Kawaguchi, Saitama, Japan
Nobuo Kimizuka

^aDepartment of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan

Abstract

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Abstract

Anionic 9,10-diphenylanthracene chromophores electrostatically bound to cationic, chiral bilayer membranes show ordered self-assembly in water. The integrity of the chromophore-accumulated aqueous bilayer membranes is ensured by multiple hydrogen-bond networks introduced in the bilayer, which allowed adaptive accommodation of the guest chromophores at the inner surface of the bilayer while maintaining their cohesive interactions. The regular chromophore alignment in the aqueous assembly is confirmed by differential scanning calorimetry, circular dichroism, and circularly polarized luminescence spectra. Excitonic migration of triplet energy occurs among the chromophores densely organized at the inner surface of the bilayer, which lead to triplet–triplet annihilation-based photon upconversion (TTA-UC). This acceptor-bilayer self-assemblies show a notably long triplet lifetime of 8.0 ms, which allows TTA-UC at sufficiently low excitation light intensity. These results demonstrate the usefulness of the simple electrostatic accumulation approach for TTA-UC chromophores where the suitable molecular design of the TTA-UC chromophore-integrated bilayer membranes plays a key role.

Key words

self-assembly - photon upconversion - triplet - triplet–triplet annihilation - bilayer membranes - energy migration

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References

References and Notes
1 Rabinowitch E. , Govindjee. Photosynthesis. Wiley; New York: 1969
2 Blankenship RE. Molecular Mechanisms of Photosynthesis. Wiley-Blackwell; Hoboken, NJ: 2014
3 Kunitake T, Shimomura M, Hashiguchi Y, Kawanaka T. J. Chem. Soc. Chem. Commun. 1985; 833
4 Tamai N, Yamazaki T, Yamazaki I. Chem. Phys. Lett. 1988; 147: 25
5 Kimizuka N, Kunitake T. J. Am. Chem. Soc. 1989; 11: 3758
6 Morita T, Kimura S, Imanishi S. J. Am. Chem. Soc. 1999; 121: 581
7 Ajayaghosh A, George SJ, Praveen VK. Angew. Chem. Int. Ed. Engl. 2003; 42: 332
8 Kayser V, Turton DA, Aggeli A, Beevers A, Reid GD, Beddard GS. J. Am. Chem. Soc. 2004; 126: 336
9 Gao M, Paul S, Schwieters CD. , et al. J. Phys. Chem. C Nanomater. Interfaces 2015; 119: 13948
10 Sethy R, Kumar J, Métivier R. , et al. Angew. Chem. Int. Ed. Engl. 2017; 56: 15053
11 Nakashima T, Kimizuka N. Adv. Mater. 2002; 14: 1113
12 Baluschev S, Miteva T, Yakutkin V, Nelles G, Yasuda A, Wegner G. Phys. Rev. Lett. 2006; 97: 143903
13 Singh-Rachford TN, Castellano FN. Coord. Chem. Rev. 2010; 254: 2560
14 Zhao JZ, Ji SM, Guo HM. RSC Advances 2011; 1: 937
15 Monguzzi A, Tubino R, Hoseinkhani S, Campione M, Meinardi F. Phys. Chem. Chem. Phys. 2012; 14: 4322
16 Simon YC, Weder C. J. Mater. Chem. 2012; 22: 20817
17 Tayebjee MJY, McCamey DR, Schmidt TW. J. Phys. Chem. Lett. 2015; 6: 2367
18 Goldschmidt JC, Fischer S. Adv. Opt. Mater. 2015; 3: 510
19 Gray V, Moth-Poulsen K, Albinsson B, Abrahamsson M. Coord. Chem. Rev. 2018; 362: 54
20 Lennartson A, Roffey A, Moth-Poulsen K. Tetrahedron Lett. 2015; 56: 1457
21 Masutani K, Morikawa MA, Kimizuka N. Chem. Commun. (Camb.) 2014; 50: 15803
22 Ishiba K, Morikawa MA, Chikara C. , et al. Angew. Chem. Int. Ed. Engl. 2015; 54: 1532
23 Duan P, Yanai N, Kimizuka N. J. Am. Chem. Soc. 2013; 135: 19056
24 Duan P, Yanai N, Nagatomi H, Kimizuka N. J. Am. Chem. Soc. 2015; 137: 1887
25 Hisamitsu S, Yanai N, Kimizuka N. Angew. Chem. Int. Ed. Engl. 2015; 54: 11550
26 Ogawa T, Yanai N, Monguzzi A, Kimizuka N. Sci. Rep. 2015; 5: 10882
27 Yanai N, Kimizuka N. Chem. Commun. (Camb.) 2016; 52: 5354
28 Kimizuka N, Yanai N, Morikawa MA. Langmuir 2016; 32: 12304
29 Wohnhaas C, Turshatov A, Mailänder V. , et al. Macromol. Biosci. 2011; 11: 772
30 Wohnhaas C, Mailänder V, Dröge M. , et al. Macromol. Biosci. 2013; 13: 1422
31 Zhou J, Liu Q, Feng W, Sun Y, Li F. Chem. Rev. 2015; 115: 395
32 Liu Q, Yang T, Feng W, Li F. J. Am. Chem. Soc. 2012; 134: 5390
33 Kim J-H, Kim J-H. J. Am. Chem. Soc. 2012; 134: 17478
34 Turshatov A, Busko D, Baluschev S, Miteva T, Landfester K. New J. Phys. 2011; 13: 083035
35 Askes SHC, Bahreman A, Bonnet S. Angew. Chem. Int. Ed. Engl. 2014; 53: 1029
36 Askes SHC, López Mora N, Harkes R. , et al. Chem. Commun. (Camb.) 2015; 51: 9137
37 Poznik V, Faltermeier V, Dick B, König B. RSC Advances 2016; 6: 41947
38 Askes SHC, Brodie P, Bruylants G, Bonnet S. J. Phys. Chem. B 2017; 121: 780
39 Kouno H, Ogawa T, Amemori S, Mahato P, Yanai N, Kimizuka N. Chem. Sci. (Camb.) 2016; 7: 5224
40 Okahata Y, Kunitake T. J. Am. Chem. Soc. 1979; 101: 5231
41 Fuhrhop JH, Wang T. Chem. Rev. 2004; 104: 2901
42 Bharmoria P, Hisamitsu S, Nagatomi H. , et al. J. Am. Chem. Soc. 2018; 140: 10848
43 Nakashima N, Ando R, Kunitake T. Bull. Chem. Soc. Jpn. 1987; 60: 1967
44 Asakuma S, Okada H, Kunitake T. J. Am. Chem. Soc. 1991; 113: 1749
45 Kimizuka N, Kawasaki T, Kunitake T. J. Am. Chem. Soc. 1993; 115: 4387
46 Kimizuka N, Kawasaki T, Hirata K, Kunitake T. J. Am. Chem. Soc. 1998; 120: 4094
47 Synthesis of 2-amino-N1,N5-bis(3-(dodecyloxy)propyl)pentanediamide (1b): Boc-L-Glutamic acid (2.83 g, 11.4 mmol), 3-(dodecyloxy)propylamine (6.2 g, 25.4 mmol) and triethyl amine (4 mL) were taken in a 500 mL round-bottomed flask and dissolved by adding 200 mL of dry dichloromethane (DCM). The mixture was stirred for 15 minutes under an ice bath. Subsequently, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (WSC, 5.51 g, 28.7 mmol) and 1-hydroxybenzotriazole hydrate (HOBt, 4.4 g, 28.7 mmol) were dissolved in 100 mL dry DCM and added dropwise to the cooled reaction mixture. The reaction mixture was stirred for 12 hours under a nitrogen atmosphere with gradual heating to room temperature. Reaction progress was monitored by thin layer chromatography (TLC). When the reaction was complete, the solvent was evaporated and the crude was washed with CHCl₃/water for 3 times. The organic layer was dried over sodium sulfate and filtered. The solvent was evaporated to give a pale-yellow crude which was further purified by column chromatography (Silica, HCl₃/MeOH) to give a colorless solid product (1a, 75% yield). The solid obtained in the first step (1a, 5.8 g, 8.5 mmol) was dissolved in dry DCM (100 mL) and treated with trifluoroacetic acid (TFA, 19 g, 167 mmol). The mixture was stirred overnight at room temperature. After reaction completion, DCM and TFA were evaporated under vacuum to give the product as a yellow oil which upon acidification with 35% HCl (10 g) gave a colorless precipitate. The obtained precipitate was purified by recrystallization from the acetone/methanol solvent mixture (1b, 58% yield). ¹H NMR (CDCl₃, 300 MHz): δ (ppm) = 8.61 (m, 3H, NH₃ ), 8.47 (t, 1H, CO-NH), 7.42 (t, 1H, CO-NH), 4.30 (m, 1H, tert.-CH), 3.51-3.01 (m, 12H), 2.60 (m, 2H), 2.25 (m, 2H), 1.95-1.68 (m, 4H), 1.66-1.02 (m, 40H), 0.90 (t, 6H, CH₃ ). (Figure S1, Supporting Information). Synthesis of 11-((18,22-dioxo-13,27-dioxa-17,23-diazanonatriacontan-19-yl)amino)-N-(2-hydroxyethyl)-N,N-dimethyl-11-oxoundecan-1-aminium (1): The deprotected intermediate product from the previous step (1b, 1.6 g, 2.7 mmol) was taken in 60 mL dry DCM and Et₃N (5 mmol) followed by addition of 11-bromo-undecanoic acid (0.82 g, 3.1 mmol) and DMAP (0.045 g, 0.37 mmol). The reaction mixture was stirred under ice-bath. A WSC (0.6 g, 3.1 mmol) solution in 20 mL dry DCM was added dropwise and stirring was continued for 12 hours at room temperature. After completion of the reaction, the solvent was evaporated, and a residue was washed by CHCl₃/water mixture. The organic phase was dried over sodium sulfate and filtered. The solvent was evaporated under vacuum, and crude was purified by recrystallization from acetone (1c, 78% yield). Finally, intermediate 1c (0.9 g, 1.0 mmol) was reacted with 2-methylaminoethanol (0.5 g, 5.5 mmol) in acetonitrile under reflux condition. The mixture was stirred for 9 hours at 80 °C. The solvent was evaporated to yield white crude which was purified by re-precipitation from MeOH solution by adding CH₃CN (45% yield). ¹H-NMR (CDCl3, 300 MHz): δ (ppm) = δ (ppm) = 7.41 (d, 1H, CO-NH), 7.30 (t, 1H, CO-NH), 6.8 (t, 1H, CO-NH), 4.37 (m, 1H, tert.-CH), 4.1 (m, 2H), 3.73 (m, 2H), 3.22-3.59 (m, 20H), 2.32-2.42 (m, 4H), 1.10-2.10 (m, 64H), 0.88 (t, 6H, CH₃ ). (Figure S2, Supporting Information). MALDI–TOF MS spectrum (dithranol matrix): Calculated molecular weight C₅₀H₁₀₁N₄O₆ ⁺ = 854.36; Obtained = 854.4. Elemental analysis calculated for C₅₀H₁₀₁N₄O₆Br + H₂O: C, 63.06; H, 10.90; Br, 8.39; N, 5.88; O, 11.76. Found: C, 63.34; H, 11.04; N, 5.98
48 Nakashima N, Fukushima H, Kunitake T. Chem. Lett. 1981; 10: 1207
49 Kawasaki T, Tokuhiro M, Kimizuka N, Kunitake T. J. Am. Chem. Soc. 2001; 123: 6792
50 Okazaki Y, Goto T, Sakaguchi R. , et al. Chem. Lett. 2016; 45: 448
51 Kumar J, Nakashima T, Kawai T. J. Phys. Chem. Lett. 2015; 6: 3445
52 Overton E. Vierteljahrsschr. Naturf. Ges. Zürich 1899; 44: 88
53 Widomska J, Raguz M, Subczynski WK. Biochim. Biophys. Acta. 2007; 1768: 2635
54 Monguzzi A, Mezyk J, Scotognella F, Tubino R, Meinardi F. Phys. Rev. B Condens. Matter Mater. Phys. 2008; 78: 195112
55 Hirata S, Totani K, Zhang J. , et al. Adv. Funct. Mater. 2013; 23: 3386
56 An Z, Zheng C, Tao Y. , et al. Nat. Mater. 2015; 14: 685

Supplementary Material

Supporting Information (PDF)