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

a  Department of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
b  School of Chemistry, The University of Manchester, Manchester, United Kingdom
,
a  Department 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
a  Department of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
,
a  Department of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
c  National Center for Nanoscience and Technology, Zhongguancun, Beijing, China
,
d  Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Nara, Japan
,
d  Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Nara, Japan
,
a  Department of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
e  PRESTO, JST, Kawaguchi, Saitama, Japan
,
a  Department of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
› Author Affiliations
Funding Information: This work was partly supported by JSPS KAKENHI Grant Numbers JP25220805, JP17H04799, JP16H06513 (Coordination Asymmetry), JP16H00844, JP14F04345.
Further Information

Publication History

Received: 28 August 2019

Accepted after revision: 24 September 2019

Publication Date:
29 November 2019 (online)


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.

Supporting Information

 
  • 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