4-{3,5-Bis[2,3,5,6-tetrafluoro-4-(piperazin-1-yl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl}benzaldehyde in the Synthesis of New Dendritic Chromophores

被引:0
作者
Ishchenko, R. A. [1 ,2 ]
Orlova, N. A. [1 ]
Shelkovnikov, V. V. [1 ,3 ]
Maksimov, A. M. [1 ]
Ryazanov, N. D. [1 ,2 ]
Berezhnaya, V. N. [1 ,2 ]
Chernonosov, A. A. [4 ]
机构
[1] Russian Acad Sci, Siberian Branch, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
[2] Novosibirsk Natl Res State Univ, Novosibirsk 630090, Russia
[3] Novosibirsk State Tech Univ, Novosibirsk 630073, Russia
[4] Russian Acad Sci, Inst Chem Biol & Fundamental Med, Siberian Branch, Novosibirsk 630090, Russia
关键词
polyfluorotriphenylpyrazolines; dicyanoisophorone; Boc-piperazine; dipolar chromophores; branched structures; DONOR BLOCKS; DERIVATIVES; PIPERAZINE; POLYMERS; DYES;
D O I
10.1134/S1070428024604722
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 4-[3,5-bis(2,3,5,6-tetrafluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]benzaldehyde with tert-butyl piperazine-1-carboxylate gave Boc-protected 4-{3,5-bis[2,3,5,6-tetrafluoro-4-(piperazin-1-yl)-phenyl]-4,5-dihydro-1H-pyrazol-1-yl}benzaldehyde. The latter reacted as a donor block with dicyanoisophorone as an acceptor block in butan-1-ol in the presence of morpholine to produce a dipolar dye with Boc-protected piperazine fragments. After removal of the Boc protection by the action of HCl, the resulting bis-piperazinium dihydrochloride was acylated with benzoyl chloride and its branched derivatives to afford new dipolar chromophores.
引用
收藏
页码:184 / 189
页数:6
相关论文
共 15 条
[1]   Synthesis of a Toolbox of Clickable Rhodamine B Derivatives [J].
Gobbo, Pierangelo ;
Gunawardene, Praveen ;
Luo, Wilson ;
Workentin, Mark S. .
SYNLETT, 2015, 26 (09) :1169-1174
[2]   Polyfluorinated triphenyl-4,5-dihydro-1H-pyrazoles with dendroid arylsulfanyl moieties as donor blocks in donor-acceptor chromophores [J].
Ishchenko, Roman A. ;
Kargapolova, Irina Yu ;
Orlova, Natalia A. ;
Shelkovnikov, Vladimir V. ;
Maksimov, Alexander M. ;
Ryazanov, Nikita D. ;
Berezhnaya, Viktoria N. ;
Chernonosov, Alexander A. .
JOURNAL OF FLUORINE CHEMISTRY, 2021, 248
[3]   Enhancement of optical, electrical, mechanical and thermal properties with Hirshfeld surface analysis of organic piperazine para-nitrophenol crystals: An effective material for NLO device fabrication [J].
Kannan, Vijayakumar ;
Maadhu, Thiyagarajan ;
Periyasamy, Palani ;
Loganathan, Rajasekaran ;
Sivaraman, Vetrivel ;
Haydullakhan, Saleem ;
Gandhiraj, Vinitha ;
Periyasamy, Purushothaman ;
Sacratees, Santhosh .
JOURNAL OF SOLID STATE CHEMISTRY, 2024, 330
[4]   Synthesis of unsymmetrical thioflavylium dyes from julolidine derivatives and polyfluorinated triphenyldihydropyrazoles [J].
Kargapolova, I. Yu. ;
Orlova, N. A. ;
Erin, K. D. ;
Shelkovnikov, V. V. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (01) :37-41
[5]  
Lemke R., 1974, Synthesis, V1974, P359, DOI [10.1055/s-1974-23322, DOI 10.1055/S-1974-23322]
[6]   Molecular engineering of organic chromophores and polymers for enhanced bulk second-order optical nonlinearity [J].
Li, Ming ;
Li, Yang ;
Zhang, Hui ;
Wang, Shiwei ;
Ao, Yuhui ;
Cui, Zhanchen .
JOURNAL OF MATERIALS CHEMISTRY C, 2017, 5 (17) :4111-4122
[7]   The Role of the Hydrogen Bond between Piperazine and Fullerene Molecules in Stabilizing Polymer:Fullerene Solar Cell Performance [J].
Li, Zerui ;
Shan, Jiankai ;
Yan, Lingpeng ;
Gu, Huimin ;
Lin, Yi ;
Tan, Hongwei ;
Ma, Chang-Qi .
ACS APPLIED MATERIALS & INTERFACES, 2020, 12 (13) :15472-15481
[8]   The design of nonlinear optical chromophores exhibiting large electro-optic activity and high thermal stability: The role of donor groups [J].
Liu, Fenggang ;
Xiao, Hongyan ;
Yang, Yuhui ;
Wang, Haoran ;
Zhang, Hua ;
Liu, Jialei ;
Bo, Shuhui ;
Zhen, Zhen ;
Liu, Xinhou ;
Qiu, Ling .
DYES AND PIGMENTS, 2016, 130 :138-147
[9]   Formyl Derivatives of Amino-Substituted Polyfluorotriphenyl-4,5-dihydro-1H-pyrazoles: Synthesis and Use as Donor Blocks of Nonlinear Optical Chromophores [J].
Shelkovnikov, V. V. ;
Orlova, N. A. ;
Kargapolova, I. Yu. ;
Erin, K. D. ;
Maksimov, A. M. ;
Chernonosov, A. A. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (10) :1504-1517
[10]   Synthesis and nonlinear optical properties of donor-acceptor dyes based on triphenylpyrazolines as a donor block and dicyanoisophorone as acceptor [J].
Shelkovnikov, V. V. ;
Kargapolova, I. Yu ;
Orlova, N. A. ;
Korotaev, S., V ;
Simanchuk, A. E. ;
Mikerin, S. L. .
RUSSIAN CHEMICAL BULLETIN, 2019, 68 (01) :92-98