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Published in: Journal of Materials Science 1/2019

20-08-2018 | Chemical routes to materials

Photothermal conversion performance of perylene diimide radical anion salts modified with tunable moieties

Authors: Qizhe Li, Wenlong Hou, Fei Peng, Hailong Wang, Shuo Zhang, Danyang Dong, Siyu Wu, Haiquan Zhang

Published in: Journal of Materials Science | Issue 1/2019

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Abstract

Among photothermal materials, perylene diimide radical anions were promising organic candidates with intense and characteristic near-infrared (NIR) absorption bands and non-fluorescence. Herein, two isolable and ambient stable bay-substituted perylene diimide radical anion salts, namely DBrPDI radical anion salt and TPPDI radical anion salt, were facilely prepared and confirmed by using a very thorough analysis based on the data from UV–Vis/NIR, FL, FTIR, EPR and NMR spectra. Subsequently, two radical anion salts were applied as photothermal conversion agents. DBrPDI radical anion salt exhibited high-performance photothermal conversion in DMF solutions, however a decline in aqueous solution. TPPDI radical anion salt with bulky moieties onto the PDI cores and amine position gave substantial evidence that the photothermal properties could be optimized and enhanced in aqueous solution by modulating the chemical structure of the photothermal conversion agent.

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Appendix
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Literature
1.
go back to reference Zha Z, Yue X, Ren Q et al (2013) form polypyrrole nanoparticles with high photothermal conversion efficiency for photothermal ablation of cancer cells. Adv Mater 25(5):777–782CrossRef Zha Z, Yue X, Ren Q et al (2013) form polypyrrole nanoparticles with high photothermal conversion efficiency for photothermal ablation of cancer cells. Adv Mater 25(5):777–782CrossRef
2.
go back to reference Li B, Wang Q, Zou R et al (2014) Cu7.2S4 nanocrystals: a novel photothermal agent with a 56.7% photothermal conversion efficiency for photothermal therapy of cancer cells. Nanoscale 6(6):3274–3282CrossRef Li B, Wang Q, Zou R et al (2014) Cu7.2S4 nanocrystals: a novel photothermal agent with a 56.7% photothermal conversion efficiency for photothermal therapy of cancer cells. Nanoscale 6(6):3274–3282CrossRef
3.
go back to reference Liu X, Li B, Fu F et al (2014) Facile synthesis of biocompatible cysteine-coated CuS nanoparticles with high photothermal conversion efficiency for cancer therapy. Dalton Trans 43(30):11709–11715CrossRef Liu X, Li B, Fu F et al (2014) Facile synthesis of biocompatible cysteine-coated CuS nanoparticles with high photothermal conversion efficiency for cancer therapy. Dalton Trans 43(30):11709–11715CrossRef
4.
go back to reference Jiao Y, Liu K, Wang G et al (2015) Supramolecular free radicals: near-infrared organic materials with enhanced photothermal conversion. Chem Sci 6(7):3975–3980CrossRef Jiao Y, Liu K, Wang G et al (2015) Supramolecular free radicals: near-infrared organic materials with enhanced photothermal conversion. Chem Sci 6(7):3975–3980CrossRef
5.
go back to reference Chen H, Shao L, Ming T et al (2010) Understanding the photothermal conversion efficiency of gold nanocrystals. Small 6(20):2272–2280CrossRef Chen H, Shao L, Ming T et al (2010) Understanding the photothermal conversion efficiency of gold nanocrystals. Small 6(20):2272–2280CrossRef
6.
go back to reference Ma Y, Tong S, Bao G et al (2013) Indocyanine green loaded SPIO nanoparticles with phospholipid-PEG coating for dual-modal imaging and photothermal therapy. Biomaterials 34(31):7706–7714CrossRef Ma Y, Tong S, Bao G et al (2013) Indocyanine green loaded SPIO nanoparticles with phospholipid-PEG coating for dual-modal imaging and photothermal therapy. Biomaterials 34(31):7706–7714CrossRef
7.
go back to reference Robinson JT, Tabakman SM, Liang Y et al (2011) Ultrasmall reduced graphene oxide with high near-infrared absorbance for photothermal therapy. J Am Chem Soc 133(17):6825–6831CrossRef Robinson JT, Tabakman SM, Liang Y et al (2011) Ultrasmall reduced graphene oxide with high near-infrared absorbance for photothermal therapy. J Am Chem Soc 133(17):6825–6831CrossRef
8.
go back to reference Tian Q, Jiang F, Zou R et al (2011) Hydrophilic Cu9S5 nanocrystals: a photothermal agent with a 25.7% heat conversion efficiency for photothermal ablation of cancer cells in vivo. ACS Nano 5(12):9761–9771CrossRef Tian Q, Jiang F, Zou R et al (2011) Hydrophilic Cu9S5 nanocrystals: a photothermal agent with a 25.7% heat conversion efficiency for photothermal ablation of cancer cells in vivo. ACS Nano 5(12):9761–9771CrossRef
9.
go back to reference Tong H, Ouyang S, Bi Y et al (2012) Nano-photocatalytic materials: possibilities and challenges. Adv Mater 24(2):229–251CrossRef Tong H, Ouyang S, Bi Y et al (2012) Nano-photocatalytic materials: possibilities and challenges. Adv Mater 24(2):229–251CrossRef
10.
go back to reference Mahata K, Frischmann PD, Würthner F (2013) Giant electroactive M4L6 tetrahedral host self-assembled with Fe(II) vertices and perylene bisimide dye edges. J Am Chem Soc 135(41):15656–15661CrossRef Mahata K, Frischmann PD, Würthner F (2013) Giant electroactive M4L6 tetrahedral host self-assembled with Fe(II) vertices and perylene bisimide dye edges. J Am Chem Soc 135(41):15656–15661CrossRef
11.
go back to reference Huang C, Barlow S, Marder SR (2011) Perylene-3, 4, 9, 10-tetracarboxylic acid diimides: synthesis, physical properties, and use in organic electronics. J Org Chem 76(8):2386–2407CrossRef Huang C, Barlow S, Marder SR (2011) Perylene-3, 4, 9, 10-tetracarboxylic acid diimides: synthesis, physical properties, and use in organic electronics. J Org Chem 76(8):2386–2407CrossRef
12.
go back to reference Zhou E, Tajima K, Yang C et al (2010) Band gap and molecular energy level control of perylene diimide-based donor–acceptor copolymers for all-polymer solar cells. J Mater Chem 20(12):2362–2368CrossRef Zhou E, Tajima K, Yang C et al (2010) Band gap and molecular energy level control of perylene diimide-based donor–acceptor copolymers for all-polymer solar cells. J Mater Chem 20(12):2362–2368CrossRef
13.
go back to reference Gosztola D, Niemczyk MP, Svec W et al (2000) Excited doublet states of electrochemically generated aromatic imide and diimide radical anions. J Phys Chem A 104(28):6545–6551CrossRef Gosztola D, Niemczyk MP, Svec W et al (2000) Excited doublet states of electrochemically generated aromatic imide and diimide radical anions. J Phys Chem A 104(28):6545–6551CrossRef
14.
go back to reference Iron MA, Cohen R, Rybtchinski B (2011) On the unexpected stability of the dianion of perylene diimide in water-a computational study. J Phys Chem A 115(10):2047–2056CrossRef Iron MA, Cohen R, Rybtchinski B (2011) On the unexpected stability of the dianion of perylene diimide in water-a computational study. J Phys Chem A 115(10):2047–2056CrossRef
15.
go back to reference Li Q, Guo H, Yang X et al (2017) Synthesis, characterization, photophysical properties and stability of bay-substituted tetrachloro-perylene diimide dianion salt by alkali treatment. Tetrahedron 73(47):6632–6636CrossRef Li Q, Guo H, Yang X et al (2017) Synthesis, characterization, photophysical properties and stability of bay-substituted tetrachloro-perylene diimide dianion salt by alkali treatment. Tetrahedron 73(47):6632–6636CrossRef
16.
go back to reference Jiao Y, Liu K, Wang G et al (2015) Supramolecular free radicals: near-infrared organic materials with enhanced photothermal conversion. Chem Sci 6(7):3975–3980CrossRef Jiao Y, Liu K, Wang G et al (2015) Supramolecular free radicals: near-infrared organic materials with enhanced photothermal conversion. Chem Sci 6(7):3975–3980CrossRef
17.
go back to reference Santos ER, Pina J, Venâncio T et al (2016) Photoinduced energy and electron-transfer reactions by polypyridine ruthenium (II) complexes containing a derivatized perylene diimide. J Phys Chem C 120(40):22831–22843CrossRef Santos ER, Pina J, Venâncio T et al (2016) Photoinduced energy and electron-transfer reactions by polypyridine ruthenium (II) complexes containing a derivatized perylene diimide. J Phys Chem C 120(40):22831–22843CrossRef
18.
go back to reference Shirman E, Ustinov A, Ben-Shitrit N et al (2008) Stable aromatic dianion in water. J Phys Chem B 112(30):8855–8858CrossRef Shirman E, Ustinov A, Ben-Shitrit N et al (2008) Stable aromatic dianion in water. J Phys Chem B 112(30):8855–8858CrossRef
19.
go back to reference Pluczyk S, Kuznik W, Lapkowski M et al (2014) The effect of the linking topology on the electrochemical and spectroelectrochemical properties of carbazolyl substituted perylene bisimides. Electrochim Acta 135:487–494CrossRef Pluczyk S, Kuznik W, Lapkowski M et al (2014) The effect of the linking topology on the electrochemical and spectroelectrochemical properties of carbazolyl substituted perylene bisimides. Electrochim Acta 135:487–494CrossRef
20.
go back to reference Schmidt D, Bialas D, Würthner F (2015) Ambient stable zwitterionic perylene bisimide-centered radical. Angew Chem Int Ed 54(12):3611–3614CrossRef Schmidt D, Bialas D, Würthner F (2015) Ambient stable zwitterionic perylene bisimide-centered radical. Angew Chem Int Ed 54(12):3611–3614CrossRef
21.
go back to reference Seifert S, Schmidt D, Würthner F (2015) An ambient stable core-substituted perylene bisimide dianion: isolation and single crystal structure analysis. Chem Sci 6(3):1663–1667CrossRef Seifert S, Schmidt D, Würthner F (2015) An ambient stable core-substituted perylene bisimide dianion: isolation and single crystal structure analysis. Chem Sci 6(3):1663–1667CrossRef
22.
go back to reference Suzuki S, Morita Y, Fukui K et al (2006) Aromaticity on the pancake-bonded dimer of neutral phenalenyl radical as studied by MS and NMR spectroscopies and NICS analysis. J Am Chem Soc 128(8):2530–2531CrossRef Suzuki S, Morita Y, Fukui K et al (2006) Aromaticity on the pancake-bonded dimer of neutral phenalenyl radical as studied by MS and NMR spectroscopies and NICS analysis. J Am Chem Soc 128(8):2530–2531CrossRef
23.
go back to reference Liu Y, Ai K, Liu J et al (2013) Dopamine-melanin colloidal nanospheres: an efficient near-infrared photothermal therapeutic agent for in vivo cancer therapy. Adv Mater 25(9):1353–1359CrossRef Liu Y, Ai K, Liu J et al (2013) Dopamine-melanin colloidal nanospheres: an efficient near-infrared photothermal therapeutic agent for in vivo cancer therapy. Adv Mater 25(9):1353–1359CrossRef
24.
go back to reference Roper DK, Ahn W, Hoepfner M (2007) Microscale heat transfer transduced by surface plasmon resonant gold nanoparticles. J Phys Chem C 111(9):3636–3641CrossRef Roper DK, Ahn W, Hoepfner M (2007) Microscale heat transfer transduced by surface plasmon resonant gold nanoparticles. J Phys Chem C 111(9):3636–3641CrossRef
25.
go back to reference Kasha M, Rawls HR, El-Bayoumi MA (1965) The exciton model in molecular spectroscopy. Pure Appl Chem 11(3–4):371–392 Kasha M, Rawls HR, El-Bayoumi MA (1965) The exciton model in molecular spectroscopy. Pure Appl Chem 11(3–4):371–392
26.
go back to reference Garcia-Yoldi I, Miller JS, Novoa JJ (2007) Structure and stability of the [TCNE] 2 2- dimers in dichloromethane solution: a computational study. J Phys Chem A 111(32):8020–8027CrossRef Garcia-Yoldi I, Miller JS, Novoa JJ (2007) Structure and stability of the [TCNE] 2 2- dimers in dichloromethane solution: a computational study. J Phys Chem A 111(32):8020–8027CrossRef
27.
go back to reference Lü JM, Rosokha SV, Kochi JK (2003) Stable (long-bonded) dimers via the quantitative self-association of different cationic, anionic, and uncharged π-radicals: structures, energetics, and optical transitions. J Am Chem Soc 125(40):12161–12171CrossRef Lü JM, Rosokha SV, Kochi JK (2003) Stable (long-bonded) dimers via the quantitative self-association of different cationic, anionic, and uncharged π-radicals: structures, energetics, and optical transitions. J Am Chem Soc 125(40):12161–12171CrossRef
28.
go back to reference Grampp G, Landgraf S, Rasmussen K et al (2002) Dimerization of organic free radicals in solution.: 1. Temperature dependent measurements. Spectrochim Acta A 58(6):1219–1226CrossRef Grampp G, Landgraf S, Rasmussen K et al (2002) Dimerization of organic free radicals in solution.: 1. Temperature dependent measurements. Spectrochim Acta A 58(6):1219–1226CrossRef
29.
go back to reference Yoneda K, Nakano M, Fukuda K et al (2014) Third-order nonlinear optical properties of one-dimensional open-shell molecular aggregates composed of phenalenyl radicals. Chem-Eur J 20(35):11129–11136CrossRef Yoneda K, Nakano M, Fukuda K et al (2014) Third-order nonlinear optical properties of one-dimensional open-shell molecular aggregates composed of phenalenyl radicals. Chem-Eur J 20(35):11129–11136CrossRef
30.
go back to reference Hu X, Lu F, Chen L et al (2017) Perylene diimide-grafted polymeric nanoparticles chelated with Gd3+ for photoacoustic/T 1-weighted magnetic resonance imaging-guided photothermal therapy. ACS Appl Mater Interface 9(36):30458–30469CrossRef Hu X, Lu F, Chen L et al (2017) Perylene diimide-grafted polymeric nanoparticles chelated with Gd3+ for photoacoustic/T 1-weighted magnetic resonance imaging-guided photothermal therapy. ACS Appl Mater Interface 9(36):30458–30469CrossRef
31.
go back to reference Sun P, Yuan P, Wang G et al (2017) High density glycopolymers functionalized perylene diimide nanoparticles for tumor-targeted photoacoustic imaging and enhanced photothermal therapy. Biomacromol 18(10):3375–3386CrossRef Sun P, Yuan P, Wang G et al (2017) High density glycopolymers functionalized perylene diimide nanoparticles for tumor-targeted photoacoustic imaging and enhanced photothermal therapy. Biomacromol 18(10):3375–3386CrossRef
Metadata
Title
Photothermal conversion performance of perylene diimide radical anion salts modified with tunable moieties
Authors
Qizhe Li
Wenlong Hou
Fei Peng
Hailong Wang
Shuo Zhang
Danyang Dong
Siyu Wu
Haiquan Zhang
Publication date
20-08-2018
Publisher
Springer US
Published in
Journal of Materials Science / Issue 1/2019
Print ISSN: 0022-2461
Electronic ISSN: 1573-4803
DOI
https://doi.org/10.1007/s10853-018-2822-2

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