Substituent Effect on the Structure and Photophysical Properties of Phenylamino- and Pyridylamino-2,1,3-Benzothiadiazoles

被引：4

作者：

Sukhikh, T. S. ^{[1
,2
]}

Khisamov, R. M. ^{[1
,2
]}

Bashirov, D. A. ^{[1
,2
]}

Kovtunova, L. M. ^{[2
,3
]}

Kuratieva, N. V. ^{[1
,2
]}

Konchenko, S. N. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, Nikolaev Inst Inorgan Chem, Siberian Branch, Novosibirsk, Russia

[2] Novosibirsk State Univ, Novosibirsk, Russia

[3] Russian Acad Sci, Boreskov Inst Catalysis, Siberian Branch, Novosibirsk, Russia

来源：

JOURNAL OF STRUCTURAL CHEMISTRY | 2019年 / 60卷 / 10期

关键词：

2; 1; 3-benzothiadiazole; crystal structure; noncovalent interactions; electronic absorption spectroscopy; photoluminescence; 2,1,3-BENZOTHIADIAZOLE DERIVATIVES; SOLAR-CELLS; COMPLEXES; FLUORESCENT; COORDINATION; CHEMISTRY; BEARING;

D O I：

10.1134/S0022476619100135

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

4-Bromo-7-phenylamino-2,1,3-benzothiadiazole (1) and 4-bromo-7-(3-pyridylamino)-2,1,3-benzo thiadiazole (2) are synthesized. Their crystal structure and photophysical properties are studied in comparison with the known phenylamino- and pyridylamino-derivatives of 2,1,3-benzothiadiazole. It is found that the aryl substituent and noncovalent interactions affect the absorption band positions and emission in a solid and a solution. It is shown that under the mechanical action on polycrystalline samples of compounds 1 and 2 a hypsochromic shift of the emission band occurs, which indicates the weakening of noncovalent intermolecular interactions.

引用

页码：1670 / 1680

页数：11

共 37 条

[1] Photophysical and photoconductive aspects of donor-acceptor low band gap conjugated copolymer [J].

Abbas, Anshad ;

Pillai, Jisha J. ;

Sreekumar, K. ;

Joseph, Rani ;

Kartha, C. Sudha .

OPTICAL MATERIALS, 2018, 84 :813-820

[2]

[Anonymous], 2000, APEX2 VERS 2 0 SAINT

[3] Novel applications of functionalized 2,1,3-benzothiadiazoles for coordination chemistry and crystal engineering [J].

Bashirov, Denis A. ;

Sukhikh, Taisiya S. ;

Kuratieva, Natalia V. ;

Chulanova, Elena A. ;

Yushina, Irina V. ;

Gritsan, Nina P. ;

Konchenko, Sergey N. ;

Zibarev, Andrey V. .

RSC ADVANCES, 2014, 4 (54) :28309-28316

[4] Recent advances in organic mechanofluorochromic materials [J].

Chi, Zhenguo ;

Zhang, Xiqi ;

Xu, Bingjia ;

Zhou, Xie ;

Ma, Chunping ;

Zhang, Yi ;

Liu, Siwei ;

Xu, Jiarui .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3878-3896

[5] Synthesis of the 4,7-Dibromo Derivative of Highly Electron-Deficient [1,2,5]Thiadiazolo[3,4-d]pyridazine and Its Cross-Coupling Reactions [J].

Chmovzh, Timofey N. ;

Knyazeva, Ekaterina A. ;

Mikhalchenko, Ludmila V. ;

Golovanov, Ivan S. ;

Amelichev, Stanislav A. ;

Rakitin, Oleg A. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (41) :5668-5677

[6] Safe Synthesis of 4,7-Dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine and Its SNAr Reactions [J].

Chmovzh, Timofey N. ;

Knyazeva, Ekaterina A. ;

Lyssenko, Konstantin A. ;

Popov, Vadim V. ;

Rakitin, Oleg A. .

MOLECULES, 2018, 23 (10)

[7] Charge-transfer chemistry of chalcogen-nitrogen π-heterocycles [J].

Chulanova, Elena A. ;

Semenov, Nikolay A. ;

Pushkarevsky, Nikolay A. ;

Gritsan, Nina P. ;

Zibarev, Andrey V. .

MENDELEEV COMMUNICATIONS, 2018, 28 (05) :453-460

[8] New Charge-Transfer Complexes with 1,2,5-Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction [J].

Chulanova, Elena A. ;

Pritchina, Elena A. ;

Malaspina, Lorraine A. ;

Grabowsky, Simon ;

Mostaghimi, Farzin ;

Beckmann, Jens ;

Bagryanskaya, Irina Yu. ;

Shakhova, Margarita V. ;

Konstantinova, Lidia S. ;

Rakitin, Oleg A. ;

Gritsan, Nina P. ;

Zibarev, Andrey V. .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (04) :852-864

[9] OLEX2: a complete structure solution, refinement and analysis program [J].

Dolomanov, Oleg V. ;

Bourhis, Luc J. ;

Gildea, Richard J. ;

Howard, Judith A. K. ;

Puschmann, Horst .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341

[10] Luminescent distyrylbenzenes: tailoring molecular structure and crystalline morphology [J].

Gierschner, Johannes ;

Park, Soo Young .

JOURNAL OF MATERIALS CHEMISTRY C, 2013, 1 (37) :5818-5832

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