水溶性苝酰亚胺化合物电子转移与长寿命自由基阴离子的生成

doi:10.12066/j.issn.1007-2861.2218

Abstract

Abstract:

A novel water-soluble perylene diimide compound, N,N'-di(polyethylene glycol)-1-(4-mercaptobenzene)-perylene-3,4,9,10-tetracarboxylic diimide (BFL), was synthesized by introducing PEG chains. Solvent-and temperature-dependent visible spectra were investigated and aggregation states were analysed. The results show that BFL in aqueous solution has only one absorption band at 530 nm, which is related to the ratio of monomer/aggregates. However, the change in the monomer/aggregates ratio with increasing concentration of BFL molecules is not obvious. Organic solvents and surfactants can disperse the compound, thereby significantly increasing the amount of the monomer. BFL can react with sodium sulfide in water;BFL is first reduced to anion radicals and then to dianions. The ability to produce a long-life free radical in the reduction reaction will make the BFL an excellent n-type material.

Key words: perylene diimide, PEG chains, electron transfer, anion radical

CLC Number:

X513

CHENG Zhengmin, ZHANG Jun, XING Feifei, ZHU Shourong. Electron transfer of water-soluble perylene diimide compound and long-life radical anion generation[J]. Journal of Shanghai University（Natural Science Edition）, 2020, 26(4): 570-577.

Figures/Tables 8

Fig. 1

Fig. 2

Fig. 3

Fig. 4

Fig. 5

Fig. 6

Fig. 7

Fig. 8

References 13

[1]	Gorl D, Zhang X, Wurthner F. Molecular assemblies of perylene bisimide dyes in water[J]. Angewandte Chemie: International Edition, 2012,51(26):6328-6348. doi: 10.1002/anie.201108690
[2]	Wurthner F, Sahamoeller C R, Fimmel B, et al. Perylene bisimide dye assemblies as archetype functional supramolecular materials[J]. Chemical Review, 2016,116(3):962-1052. doi: 10.1021/acs.chemrev.5b00188
[3]	Kozma E, Catellani M. Perylene diimides based materials for organic solar cells[J]. Dyes and Pigments, 2013,98(1):160-179. doi: 10.1016/j.dyepig.2013.01.020
[4]	Gao B X, Li H X, Liu H M, et al. Water-soluble and fluorescent dendritic perylene bisimides for live-cell imaging[J]. Chemical Communications, 2011,47(13):3894-3896. doi: 10.1039/c1cc00058f
[5]	Kavery E, Nagarajan N, Paramaguru G, et al. Synjournal, characterization and binding interactions of amino acids coupled perylene diimides with colloidal doped and undoped TiO$_{2}$[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015,146:13-23. doi: 10.1016/j.saa.2015.03.062
[6]	Quintana J A, Villalvilla J M, Pena D L, et al. Singular temperatures connected to charge transport mechanism transitions in perylene bisimides from steady-state photocurrent measurements[J]. Journal of Physical Chemistry C, 2015,119(25):14023-14028. doi: 10.1021/acs.jpcc.5b03152
[7]	Tang T, Peneva K, Muellen K, et al. Photophysics of water soluble perylene diimides in surfactant solutions[J]. Journal of Physical Chemistry A, 2007,111(42):10609-10614. doi: 10.1021/jp073782s
[8]	Ajayakumar M R, Asthana D, Mukhopadhyay P. Core-modified naphthalenediimides generate persistent radical anion and cation: new panchromatic nir probes[J]. Organic Letters, 2012,14(18):4822-4825. doi: 10.1021/ol302140x pmid: 22954312
[9]	高薇, 席亚楠, 薄福丽, 等. 水溶性苝酰亚胺功能荧光染料的合成与性质[J]. 河北大学学报 (自然科学版), 2016,36(2):1000-1565.
[10]	Zhong L N, Xing F F, Shi W, et al. Synjournal, spectra, and electron-transfer reaction of aspartic acid-functionalized water-soluble perylene bisimide in aqueous solution[J]. ACS Applied Materials & Interfaces, 2013,5(8):3401-3407. doi: 10.1021/am4004446 pmid: 23506346
[11]	Ford W E. Photochemistry of 3,4,9,10-perylenetetracarboxylic dianhydride dyes: visible absorption and fluorescence of the di(glycyl)imide derivative monomer and dimer in basic aqueous solutions[J]. Journal of Photochemistry, 1987,37(1):189-204. doi: 10.1016/0047-2670(87)85040-2
[12]	Wang J, Zhong S, Duan W, et al. Fluorinated perylene diimides: synjournal, electrochemical-photophysical properties, and cellular imaging[J]. Tetrahedron Letters, 2015,56(6):824-827. doi: 10.1016/j.tetlet.2014.12.112
[13]	Che Y, Datar A, Yang X, et al. Enhancing one-dimensional charge transport through intermolecular $\pi $-electron delocalization: conductivity improvement for organic nanobelts[J]. Journal of American Chemical Society, 2007,129(20):6354-6355. doi: 10.1021/ja070164g

Electron transfer of water-soluble perylene diimide compound and long-life radical anion generation

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 8

References 13

Related Articles 4

Recommended Articles

Metrics

Comments

[1]	HUANG Yining, ZHANG Shenghua, XU Binhua, ZHU Jiqi, MAO Wenwen, FENG Jialiang. Mass concentrations and seasonal variations of carbon, nitrogen and sulphur in PM_2.5 in Shanghai [J]. Journal of Shanghai University（Natural Science Edition）, 2020, 26(3): 433-442.
[2]	Huanbing CHEN, Yi CHANG, Shenghua ZHANG, Yining HUANG, Jialiang FENG. Characteristics and sources of alkanes in PM$_\textbf{2.5}$ in Yiwu City [J]. Journal of Shanghai University（Natural Science Edition）, 2019, 25(4): 566-575.
[3]	Yu SHANG, Tiantian WANG, Meiying WU, Lu WANG, Huixin HE, Jing AN. Cytotoxicity in SH-SY5Y cells induced by $O_{3}$-oxidized black carbon particles [J]. Journal of Shanghai University（Natural Science Edition）, 2019, 25(4): 550-557.
[4]	XIA Xiaoyu, WU Minghong, XU Gang, SUN Rui, TANG Liang. Distribution and profiles of perfluorinated compounds in surrounding surface water around a specific point-source in Shanghai [J]. Journal of Shanghai University（Natural Science Edition）, 2019, 25(2): 266-274.