Synthesis and photophysical activity of 6-substituted isocoumarins

被引：1

作者：

Fedina, Elena S. ^{[1
,2
]}

Arsenov, Mikhail A. ^{[1
]}

Isakovskaya, Kseniya L. ^{[1
]}

Muratov, Dmitry, V ^{[1
]}

Loginov, Dmitry A. ^{[1
,3
]}

机构：

[1] A N Nesmeyanov Inst Organoelement Cpds, Russian Acad Sci, Moscow 119334, Russia

[2] Sirius Univ Sci & Technol, Soci 354349, Russia

[3] G V Plekhanov Russian Univ Econ, Moscow 117997, Russia

来源：

MENDELEEV COMMUNICATIONS | 2024年 / 34卷 / 01期

基金：

俄罗斯科学基金会;

关键词：

C-H annulation; cross-coupling; isocoumarins; luminescence; homogeneous catalysis; ALKYNES; ACIDS;

D O I：

10.1016/j.mencom.2024.01.032

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

6 -Substituted isocoumarins with aryl, alkynyl, and diphenylamino substituents were synthesized from 4-bromobenzoic acid by annulation with tolane via rhodium -catalyzed C-H activation followed by palladium -catalyzed cross -coupling reactions. The compounds obtained exhibit luminescence emission in the violet-blue region (370-480 nm) with quantum yields up to 95% (for the diphenylamino derivative). Aggregation of biphenyl -substituted isocoumarin leads to a strong batho chromic shift (by 80 nm) of emission as a result of intermolecular p-p stacking interactions.

引用

页码：107 / 109

页数：3

共 27 条

[1] Arsenov M. A., 2021, INEOS OPEN, V4, P133, DOI DOI 10.32931/IO2117R
[2] Synthesis of isocoumarins and PAHs with electron-withdrawing substituents: Impact of the substituent nature on the photophysical behavior
Arsenov, Mikhail A.
V. Fedorov, Yury
V. Muratov, Dmitry
V. Nelyubina, Yulia
Loginov, Dmitry A.
[J]. DYES AND PIGMENTS, 2022, 206
[3] Tandem C-H Annulation Reaction of Benzaldehydes and Aminobenzoic Acids with Two Equivalents of Alkyne toward Isocoumarin-Conjugated Isoquinolinium Salts: A Family of Organic Luminophores
Arsenov, Mikhail A. A.
Muratov, Dmitry V. V.
Nelyubina, Yulia V. V.
Loginov, Dmitry A. A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13) : 9360 - 9371
[4] Coumarin-Based Small-Molecule Fluorescent Chemosensors
Cao, Duxia
Liu, Zhiqiang
Verwilst, Peter
Koo, Seyoung
Jangjili, Paramesh
Kim, Jong Seung
Lin, Weiying
[J]. CHEMICAL REVIEWS, 2019, 119 (18) : 10403 - 10519
[5] OLEX2: a complete structure solution, refinement and analysis program
Dolomanov, Oleg V.
Bourhis, Luc J.
Gildea, Richard J.
Howard, Judith A. K.
Puschmann, Horst
[J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 : 339 - 341
[6] Carboxylic Acids as Directing Groups for C-H Bond Functionalization
Drapeau, Martin Pichette
Goossen, Lukas J.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (52) : 18654 - 18677
[7] New electron-deficient 2,1,3-benzothiadiazole-cored donor-acceptor compounds: synthesis, photophysical and electroluminescent properties
Gribanov, Pavel S.
Loginov, Dmitry A.
Lypenko, Dmitry A.
Dmitriev, Artem V.
Tokarev, Sergey D.
Aleksandrov, Alexey E.
Tameev, Alexey R.
Chernyadyev, Andrey Yu.
Osipov, Sergey N.
[J]. MENDELEEV COMMUNICATIONS, 2023, 33 (05) : 701 - 704
[8] Rhodium-Catalyzed C-H Activation/Annulation of Aryl Hydroxamates with Benzothiadiazol-Containing Acetylenes: Access to Isoquinoline-Bridged Donor-Acceptor Luminophores
Gribanov, Pavel S.
Vorobyeva, Daria V.
Tokarev, Sergey D.
Petropavlovskikh, Dmitry A.
Loginov, Dmitry A.
Nefedov, Sergey E.
Dolgushin, Fedor M.
Osipov, Sergey N.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (13)
[9] Synthesis and optical properties of novel unsymmetrically substituted benzothiadiazole-based luminophores
Gribanov, Pavel S.
Lypenko, Dmitry A.
Dmitriev, Artem V.
Pozin, Sergey I.
Topchiy, Maxim A.
Asachenko, Andrey F.
Loginov, Dmitry A.
Osipov, Sergey N.
Khim, Ser.
[J]. MENDELEEV COMMUNICATIONS, 2021, 31 (01) : 33 - 35
[10] Functional isocoumarin-containing polymers synthesized by rhodium-catalyzed oxidative polycoupling of aryl diacid and internal diyne
Han, Ting
Deng, Haiqin
Yu, Chris Y. Y.
Gui, Chen
Song, Zhegang
Kwok, Ryan T. K.
Lam, Jacky W. Y.
Tang, Ben Zhong
[J]. POLYMER CHEMISTRY, 2016, 7 (14) : 2501 - 2510

← 1 2 3 →