Synthesis, properties and application of novel 5,6,5,6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF2) fluorescent dyes:BOPYPYs

被引：2

作者：

Xindong Jiang ^{[1
,2
]}

Shuai Yue ^{[1
]}

Kepeng Chen ^{[3
]}

Zhumei Shao ^{[1
]}

Chen Li ^{[1
]}

Yajun Su ^{[1
]}

Jianzhang Zhao ^{[3
]}

机构：

[1] College of Applied Chemistry, Shenyang University of Chemical Technology

[2] Department of Chemistry, Graduate School of Science, Hiroshima University

[3] State Key Laboratory of Fine Chemicals, Dalian University of Technology

来源：

Chinese Chemical Letters | 2019年 / 30卷 / 12期

基金：

中国国家自然科学基金;

关键词：

BOPYPY; Pyrazine; Fluorescent dye; Unsymmetric; pH;

D O I：

暂无

中图分类号：

TQ617.3 [荧光、磷光染料]; O641.4 [络合物化学（配位化学）]; TP212.14 [];

学科分类号：

070304 ; 0803 ; 0817 ; 081704 ;

摘要：

Novel 5,6,5,6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF2) fluorescent dyes(BOPYPYs) were obtained by reaction of pyrrole-2-carboxaldehyde with 1-(pyrazin-2-yl)hydrazine in the presence of Et3N-BF3·Et2O for the first time.The absorption maxima of pyrazine-fused BOPYPY are obviously bathochromic shifts,in contrast to those of the reported BOPPY,indicating that the discrepant substitute groups between pyridine and pyrazine result in the remarkable wavelength difference.The new series of BO PYPYs possess high molar extinction coefficients,high fluorescence quantum yields,and larger Stokes shifts.A Knoevenagel reaction of BOPYPY with 4-dimethylaminobenzaldehyde smoothly produced the dye with the extension of π-conjugation.Dimethylamino-containing BOPYPY as a pH-responsive fluorescent sensor could detect pH value.

引用

页码：2271 / 2273

页数：3

共 11 条

[1] Synthesis, properties and application of novel 5,6,5,6-tetracyclic pyrazine/pyrrole-fused unsymmetric bis(BF2) fluorescent dyes: BOPYPYs
Jiang, Xindong
Yue, Shuai
Chen, Kepeng
Shao, Zhumei
Li, Chen
Su, Yajun
Zhao, Jianzhang
[J]. CHINESE CHEMICAL LETTERS, 2019, 30 (12) : 2271 - 2273
[2] Intensely blue-fluorescent 2,5-bis(benzoimidazol-2-yl)pyrazine dyes with improved solubility: their synthesis, fluorescent properties, and application as microenvironment polarity probes
Saito, Ryota
Matsumura, Yuriko
Suzuki, Saori
Okazaki, Naoki
[J]. TETRAHEDRON, 2010, 66 (42) : 8273 - 8279
[3] A NOVEL WATER-SOLUBLE FLUORESCENT-PROBE - SYNTHESIS, LUMINESCENCE AND BIOLOGICAL PROPERTIES OF THE SODIUM-SALT OF THE 4-SULFONATO-3,3',5,5'-TETRAMETHYL-2,2'-PYRROMETHEN-1,1'-BF2 COMPLEX
WORIES, HJ
KOEK, JH
LODDER, G
LUGTENBURG, J
FOKKENS, R
DRIESSEN, O
MOHN, GR
[J]. RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1985, 104 (11): : 288 - 291
[4] Synthesis and properties of bis(pyrazino[2′,3′:4,5]imidazole)-fused 1,2,5,6-tetrahydro-1,4,5,8,9,10-hexaazaanthracenes: a new fluorescent nitrogen-rich heterocycle
Hachiya, Sojiro
Hashizume, Daisuke
Maki, Shojiro
Niwa, Haruki
Hirano, Takashi
[J]. TETRAHEDRON LETTERS, 2010, 51 (10) : 1401 - 1403
[5] Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes
Adel Alimmari
Dušan Mijin
Radovan Vukićević
Bojan Božić
Nataša Valentić
Vesna Vitnik
Željko Vitnik
Gordana Ušćumlić
[J]. Chemistry Central Journal, 6
[6] Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes
Alimmari, Adel
Mijin, Dusan
Vukicevic, Radovan
Bozic, Bojan
Valentic, Natasa
Vitnik, Vesna
Vitnik, Zeljko
Uscumlic, Gordana
[J]. CHEMISTRY CENTRAL JOURNAL, 2012, 6
[7] A Fluorescent Blue Phosphazene Dye: Synthesis, Structure and Optical Properties of 1,6-Bis(Dimethylamino)-2,5,7,10-Tetraazo-1,6λ5-Diphosphapyrene
Lebkuecher, Anna
Rybina, Arina
Herten, Dirk-Peter
Huebner, Olaf
Wadepohl, Hubert
Kaifer, Elisabeth
Himmel, Hans-Joerg
[J]. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2011, 637 (05): : 547 - 555
[8] Domino protocol for the synthesis of diversely functionalized derivatives of a novel fused pentacyclic antioxidant/anticancer fluorescent scaffold: Pyrazolo[5",1":2',3']pyrimido[4',5':5,6][1,4]thiazino[2,3-b]quinoxaline
Sheikhi-Mohammareh, Seddigheh
Oroojalian, Fatemeh
Beyzaei, Hamid
Moghaddam-Manesh, Mohammadreza
Salimi, Alireza
Azizollahi, Fatemeh
Shiri, Ali
[J]. TALANTA, 2023, 262
[9] Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-(4-methoxyphenyl)-3-cyano-2-pyridone dyes: Hydrazone-azo tautomeric analysis
Alimmari, Adel
Bozic, Bojan
Mijin, Dusan
Marinkovic, Aleksandar
Valentic, Natasa
Uscumlic, Gordana
[J]. ARABIAN JOURNAL OF CHEMISTRY, 2015, 8 (02) : 269 - 278
[10] SYNTHESIS AND SPECTRAL PROPERTIES OF THE NOVEL DICATIONIC BIMETALLIC PHOSPHINE-BRIDGED COMPOUNDS [W2I2(MU-L-L)(CO)2(DPPM)2(ETA-2-MEC2ME)2][BF4]2 (DPPM = PH2P(CH2)PPH2 - L-L = PH2P(CH2)NPPH2, N = 1-6 OR [FE(ETA-5-C5H4PPH2)2])
BAKER, PK
FLOWER, KR
[J]. POLYHEDRON, 1990, 9 (20) : 2507 - 2510

← 1 2 →