Multicomponent Synthesis of Luminescent Iminoboronates

被引：7

作者：

Guieu, Samuel ^{[1
,2
]}

Esteves, Catia I. C. ^{[1
]}

Rocha, Joao ^{[2
]}

Silva, Artur M. S. ^{[1
]}

机构：

[1] Univ Aveiro, Dept Chem, LAQV REQUIMTE, P-3810193 Aveiro, Portugal

[2] Univ Aveiro, Dept Chem, CICECO Aveiro Inst Mat, P-3810193 Aveiro, Portugal

来源：

MOLECULES | 2020年 / 25卷 / 24期

关键词：

anthranilic acid; 2-hydroxybenzaldehydes; phenylboronic acid; fluorescence; aggregation-induced emission enhancement; AGGREGATION-INDUCED EMISSION; DERIVATIVES; COMPLEXES; HETEROCYCLES;

D O I：

10.3390/molecules25246039

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A family of iminoboronates was prepared through a one-pot multicomponent reaction, starting from boronic acid, anthranilic acid, and different salicylaldehydes. Their synthesis was straightforward and the complexes were obtained in good to excellent yields. Their photophysical properties were assessed in a diluted solution, and the complexes proved to be faintly luminescent. These chelates demonstrated remarkable Aggregation-Induced Emission Enhancement, which was rationalized using crystal structures.

引用

页数：9

共 27 条

[1] Microwave-assisted reaction between 2-aminobenzoic acids, 2-hydroxybenzaldehydes, and arylboronic acids: a one-pot three-component synthesis of bridgehead bicyclo[4.4.0]boron heterocycles [J].

Adib, Mehdi ;

Sheikhi, Ehsan ;

Bijanzadeh, Hamid Reza ;

Zhu, Long-Guan .

TETRAHEDRON, 2012, 68 (16) :3377-3383

[2] Electronic and Functional Scope of Boronic Acid Derived Salicylidenehydrazone (BASHY) Complexes as Fluorescent Dyes [J].

Alcaide, Maria M. ;

Santos, Fabio M. F. ;

Pais, Vania F. ;

Carvalho, Joana Ines ;

Collado, Daniel ;

Perez-Inestrosa, Ezequiel ;

Arteaga, Jesus F. ;

Bosca, Francisco ;

Gois, Pedro M. P. ;

Pischel, Uwe .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (14) :7151-7158

[3] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[4] Δ1-pyrroline based boranyls: Synthesis, crystal structures and luminescent properties [J].

Cardona, Francisco ;

Rocha, Joao ;

Silva, Artur M. S. ;

Guieu, Samuel .

DYES AND PIGMENTS, 2014, 111 :16-20

[5] Synthesis, structures and luminescent behaviour of tridentate salicylaldiminato-type borate complexes [J].

Christou, Victor ;

Watkins, Scott E. ;

McCann, Ruth ;

Redshaw, Carl ;

Elsegood, Mark R. J. .

INORGANICA CHIMICA ACTA, 2010, 363 (06) :1173-1178

[6] Porphyrin-boron diketonate dyads [J].

Costa, Leticia D. ;

Guieu, Samuel ;

Rocha, Joao ;

Silva, Artur M. S. ;

Tome, Augusto C. .

NEW JOURNAL OF CHEMISTRY, 2017, 41 (05) :2186-2192

[7]

DEMAS JN, 1971, J PHYS CHEM-US, V75, P991, DOI 10.1021/j100678a001

[8] AIE-active boron complexes based on benzothiazole-hydrazone chelates [J].

Duan, Wenzeng ;

Liu, Qingsong ;

Huo, Yanmin ;

Cui, Jichun ;

Gong, Shuwen ;

Liu, Zhipeng .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (27) :4977-4984

[9] Recent development of boronic acid-based fluorescent sensors [J].

Fang, Guiqian ;

Wang, Hao ;

Bian, Zhancun ;

Sun, Jie ;

Liu, Aiqin ;

Fang, Hao ;

Liu, Bo ;

Yao, Qingqiang ;

Wu, Zhongyu .

RSC ADVANCES, 2018, 8 (51) :29400-29427

[10] Luminescent Materials: Locking π-Conjugated and Heterocyclic Ligands with Boron(III) [J].

Frath, Denis ;

Massue, Julien ;

Ulrich, Gilles ;

Ziessel, Raymond .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (09) :2290-2310

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