Dipolar Dyes with a Pyrrolo[2,3-b]quinoxaline Skeleton Containing a Cyano Group and a Bridged Tertiary Amino Group: Synthesis, Solvatofluorochromism, and Bioimaging

被引：9

作者：

Lukasiewicz, Lukasz G. ^{[1
]}

Deperasinska, Irena ^{[2
]}

Poronik, Yevgen M. ^{[1
]}

Jun, Yong Woong

Banasiewicz, Marzena ^{[2
]}

Kozankiewicz, Boleslaw ^{[2
]}

Ahn, Kyo Han ^{[3
]}

Gryko, Daniel T. ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

[2] Polish Acad Sci, Inst Phys, Al Lotnikow 32-46, PL-02668 Warsaw, Poland

[3] POSTECH, Dept Chem, 77 Cheongam Ro, Pohang 37673, Gyungbuk, South Korea

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2016年 / 11卷 / 11期

基金：

新加坡国家研究基金会;

关键词：

dyes/pigments; fluorescence; fused-ring systems; heterocycles; photophysics; 2-PHOTON FLUORESCENT-PROBES; BIFUNCTIONAL NUCLEOPHILIC BEHAVIOR; OPTICAL-PROPERTIES; LIPID RAFTS; LIVE CELLS; ACIDIC VESICLES; NITRIC-OXIDE; PUSH; FLUOROPHORES; DESIGN;

D O I：

10.1002/asia.201600257

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two strongly polarized dipolar chromophores possessing a cyclic tertiary amino group at one terminus of the molecule and a CN group at the opposite terminus were designed and synthesized. Their rigid skeleton contains the rarely studied pyrrolo[2,3-b]quinoxaline ring system. The photophysical properties of these regioisomeric dyes were different owing to differing pi conjugation between the CN group and the electron-donor moiety. These dipolar molecules showed very intense emission, strong solvatofluorochromism, and sufficient two-photon brightness for bioimaging. One of these regioisomeric dyes, namely, 11-carbonitrile-2,3,4,5,6,7-hexahydro-1H-3a, 8,13,13b-tetraazabenzo[b]cyclohepta[1,2,3-jk]fluorene, was successfully utilized in two-photon imaging of mouse organ tissues and showed distinct tissue morphology with high resolution.

引用

页码：1718 / 1724

页数：7

共 50 条

[1] QUINOXALINES .21. SYNTHESIS OF 2-SUBSTITUTED FURO[2,3-B]QUINOXALINE AND 2-SUBSTITUTED PYRROLO[2,3-B]QUINOXALINE
IIJIMA, C
HAYASHI, E
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1977, 97 (07): : 712 - 718
[2] Organic dyes containing indolo[2,3-b]quinoxaline as a donor: synthesis, optical and photovoltaic properties
Venkateswararao, A.
Tyagi, Payal
Thomas, K. R. Justin
Chen, Ping-Wei
Ho, Kuo-Chuan
TETRAHEDRON, 2014, 70 (36) : 6318 - 6327
[3] Synthesis and computational evaluation of the antioxidant activity of pyrrolo[2,3-b]quinoxaline derivatives
Nguyen, Nguyen Tran
Dai, Vo Viet
Mechler, Adam
Van Meervelt, Luc
Hoa, Nguyen Thi
Vo, Quan V.
RSC ADVANCES, 2024, 14 (34) : 24438 - 24446
[4] Synthesis, crystal structures, and optical properties of the π-π interacting pyrrolo[2,3-b] quinoxaline derivatives containing 2-thienyl substituent
Goszczycki, Piotr
Stadnicka, Katarzyna
Brela, Mateusz Z.
Grolik, Jaroslaw
Ostrowska, Katarzyna
JOURNAL OF MOLECULAR STRUCTURE, 2017, 1146 : 337 - 346
[5] Synthesis of Unexpected Pyrrolo[2,3-b]quinoxaline-2-carbaldehydes via Sonogashira Coupling Reaction
Keivanloo, Ali
Bakherad, Mohammad
Rahimi, Amin
SYNTHESIS-STUTTGART, 2010, (10): : 1599 - 1602
[6] Synthesis, structure, and photophysical properties of luminescent zinc and cadmium complexes containing 2-pyridyl-substituted pyrrolo[2,3-b]quinoxaline
Ostrowska, Katarzyna
Stadnicka, Katarzyna
Gryl, Marlena
Musielak, Bogdan
Witek, Lukasz J.
Bochenska, Oliwia
POLYHEDRON, 2017, 133 : 294 - 301
[7] Practical Synthesis of Chromeno[ 2,3-b] indole Skeleton via an Aldehyde Group Insertion/Aromatization Strategy
Liu, Jianming
Liu, Na
Yue, Yuanyuan
Wang, Yanyan
Chen, Kaige
Zhang, Jia
Zhao, Shufang
Zhuo, Kelei
CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (04) : 401 - 404
[8] ACETALS OF LACTAMS AND ACIDAMIDES .19. SYNTHESIS OF 3-CYANO-6-DIMETHYL-AMINOPYRIDONE-2 AND PYRROLO[2,3-B]PYRIDINE, PYRIDO[2,3-B]PYRIDINE AND AZEPINO[2,3-B]PYRIDINE DERIVATIVES
GRANIK, VG
BELYAYEVA, OY
GLUSHKOV, RG
VLASOVA, TF
ANISIMOVA, OS
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1977, (08): : 1106 - 1109
[9] Chelate Ring Size Effect as a Factor of Selective Fluorescent Recognition of Zn2+ Ions by Pyrrolo[2,3-b]quinoxaline with a Substituted 2-Pyridyl Group Receptor
Ostrowska, Katarzyna
Musielak, Bogdan
Szneler, Edward
Dudek, Lukasz
Gryl, Marlena
Stadnicka, Katarzyna
INORGANIC CHEMISTRY, 2015, 54 (17) : 8423 - 8435
[10] A rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo[2,3-b]indole skeleton, a building block for 10b-hydroxy-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-diones
Ley, SV
Cleator, E
Hewitt, PR
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (20) : 3492 - 3494

← 1 2 3 4 5 →