Unexpectedly Long Lifetime of the Excited State of Benzothiadiazole Derivative and Its Adducts with Lewis Acids

被引：10

作者：

Sukhikh, Taisiya S. ^{[1
]}

Khisamov, Radmir M. ^{[1
]}

Konchenko, Sergey N. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, Nikolaev Inst Inorgan Chem, Novosibirsk 630090, Russia

来源：

MOLECULES | 2021年 / 26卷 / 07期

基金：

俄罗斯科学基金会;

关键词：

benzothiadiazole; Lewis acid; photoluminescence; single crystal X-ray diffraction; phosphorescence;

D O I：

10.3390/molecules26072030

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：

We report a study of photoluminescent properties of 4-bromo-7-(3-pyridylamino)-2,1,3-benzothiadiazole (Py-btd) and its novel Lewis adducts: (PyH-btd)(2)(ZnCl4) and [Cu2Cl2(Py-btd)(2){PPO}(2)]center dot 2C(7)H(8) (PPO = tetraphenyldiphosphine monoxide), whose crystal structure was determined by X-ray diffraction analysis. Py-btd exhibits a lifetime of 9 microseconds indicating its phosphorescent nature, which is rare for purely organic compounds. This phenomenon arises from the heavy atom effect: the presence of a bromine atom in Py-btd promotes mixing of the singlet and triplet states to allow efficient singlet-to-triplet intersystem crossing. The Lewis adducts also feature a microsecond lifetime while emitting in a higher energy range than free Py-btd, which opens up the possibility to color-tune luminescence of benzothiadiazole derivatives.

引用

页数：12

共 56 条

[1] Toward reliable density functional methods without adjustable parameters: The PBE0 model [J].

Adamo, C ;

Barone, V .

JOURNAL OF CHEMICAL PHYSICS, 1999, 110 (13) :6158-6170

[2]

[Anonymous], 2017, BRUKER APEX3 SOFTWAR

[3] Synthesis of 2,2′-[2,2′-(arenediyl)bis(anthra[2,3-b]thiophene-5,10-diylidene)] tetrapropanedinitriles and their performance as non-fullerene acceptors in organic photovoltaics [J].

Baranov, Denis S. ;

Krivenko, Olga L. ;

Kazantsev, Maxim S. ;

Nevostruev, Danil A. ;

Kobeleva, Elena S. ;

Zinoviev, Vladimir A. ;

Dmitriev, Alexey A. ;

Gritsan, Nina P. ;

Kulik, Leonid, V .

SYNTHETIC METALS, 2019, 255

[4] The interplay between fluorescence and phosphorescence with luminescent gold(I) and gold(III) complexes bearing heterocyclic arylacetylide ligands [J].

Chan, Kaai Tung ;

Tong, Glenna So Ming ;

To, Wai-Pong ;

Yang, Chen ;

Du, Lili ;

Phillips, David Lee ;

Che, Chi-Ming .

CHEMICAL SCIENCE, 2017, 8 (03) :2352-2364

[5] Novel white-light-emitting polyfluorenes with benzothiadiazole and Ir complex on the backbone [J].

Chen, Qiliang ;

Liu, Nanliu ;

Ying, Lei ;

Yang, Wei ;

Wu, Hongbin ;

Xu, Wei ;

Cao, Yong .

POLYMER, 2009, 50 (06) :1430-1437

[6] Lewis Ambiphilicity of 1,2,5-Chalcogenadiazoles for Crystal Engineering: Complexes with Crown Ethers [J].

Chulanova, Elena A. ;

Radiush, Ekaterina A. ;

Shundrina, Inna K. ;

Bagryanskaya, Irina Yu ;

Semenov, Nikolay A. ;

Beckmann, Jens ;

Gritsan, Nina P. ;

Zibarev, Andrey, V .

CRYSTAL GROWTH & DESIGN, 2020, 20 (09) :5868-5879

[7] TOPAS and TOPAS-Academic: an optimization program integrating computer algebra and crystallographic objects written in C plus [J].

Coelho, Alan A. .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2018, 51 :210-218

[8] 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

[9] Reversible mechanochromism in dipyridylamine-substituted unsymmetrical benzothiadiazoles [J].

Gautam, Prabhat ;

Maragani, Ramesh ;

Mobin, Shaikh M. ;

Misra, Rajneesh .

RSC ADVANCES, 2014, 4 (94) :52526-52529

[10] Benzothiadiazole-based photosensitizers for efficient and stable dye-sensitized solar cells and 8.7% efficiency semi-transparent mini-modules [J].

Godfroy, Maxime ;

Liotier, Johan ;

Mwalukuku, Valid M. ;

Joly, Damien ;

Huaulme, Quentin ;

Cabau, Lydia ;

Aumaitre, Cyril ;

Kervella, Yann ;

Narbey, Stephanie ;

Oswald, Frederic ;

Palomares, Emilio ;

Gonzalez Flores, Carlos A. ;

Oskam, Gerko ;

Demadrille, Renaud .

SUSTAINABLE ENERGY & FUELS, 2021, 5 (01) :144-153

← 1 2 3 4 5 6 →