Synthesis and Optical Properties of Fluorinated Tetraphenylethylenes

被引:4
作者
Zhang, Zhenglin [1 ]
Lieu, Thien [1 ]
Wang, Xiqu [1 ]
Daugulis, Olafs [1 ]
Miljanic, Ognjen S. [1 ]
机构
[1] Univ Houston, Dept Chem, 3585 Cullen Blvd 112, Houston, TX 77204 USA
基金
美国国家科学基金会;
关键词
copper; C-C coupling; fluorination; phenanthrene; palladium; photocyclization; AGGREGATION-INDUCED EMISSION; PHOTOCYCLIZATION; DERIVATIVES; RESTRICTION; MECHANISM; BOND;
D O I
10.1002/cptc.202200011
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Four extensively fluorinated tetraphenylethylenes (TPE) and one extensively fluorinated triphenylethylene have been synthesized using combinations of copper-catalyzed C-H functionalization reactions and Stille coupling reactions. Surprisingly, in contrast to the parent TPE, these compounds show little to no aggregation-induced emission (AIE). Instead, photocyclization into fluorinated phenanthrene products occurs. Effects of solvent and oxygen on the yield and selectivity of this photo-cyclization have been examined.
引用
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页数:5
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共 54 条
[31]  
Mallory F. B., 2005, Organic Reactions, P1, DOI [DOI 10.1002/0471264180.0R030.01, DOI 10.1002/0471264180.OR030.01]
[32]   PHOTOCHEMISTRY OF STILBENES .8. ELIMINATIVE PHOTOCYCLIZATION OF ORTHO-METHOXYSTILBENES [J].
MALLORY, FB ;
RUDOLPH, MJ ;
OH, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4619-4626
[33]   Aggregation-Induced Emission: Together We Shine, United We Soar! [J].
Mei, Ju ;
Leung, Nelson L. C. ;
Kwok, Ryan T. K. ;
Lam, Jacky W. Y. ;
Tang, Ben Zhong .
CHEMICAL REVIEWS, 2015, 115 (21) :11718-11940
[34]   PHOTOCYCLIZATION OF ORTHO-HALOSTILBENES [J].
OLSEN, RJ ;
PRUETT, SR .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5457-5460
[35]   The effect of vicinyl olefinic halogens on cross-coupling reactions using Pd(0) catalysis [J].
Organ, MG ;
Ghasemi, H ;
Valente, C .
TETRAHEDRON, 2004, 60 (42) :9453-9461
[36]   How does tetraphenylethylene relax from its excited states? [J].
Prlj, Antonio ;
Doslic, Nada ;
Corminboeuf, Clemence .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2016, 18 (17) :11606-11609
[37]   Locking the phenyl rings of tetraphenylethene step by step: understanding the mechanism of aggregation-induced emission [J].
Shi, Junqing ;
Chang, Ning ;
Li, Cuihong ;
Mei, Ju ;
Deng, Chunmei ;
Luo, Xiaoliang ;
Liu, Zhengping ;
Bo, Zhishan ;
Dong, Yong Qiang ;
Tang, Ben Zhong .
CHEMICAL COMMUNICATIONS, 2012, 48 (86) :10675-10677
[38]   Synthesis of Derivatives of Phenanthrene and Helicene by Improved Procedures of Photocyclization of Stilbenes [J].
Talele, Harish R. ;
Gohil, Monik J. ;
Bedekar, Ashutosh V. .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2009, 82 (09) :1182-1186
[39]   Mechanisms of fluorescence quenching in prototypical aggregation-induced emission systems: excited state dynamics with TD-DFTB [J].
Tran, Thierry ;
Prlj, Antonio ;
Lin, Kun-Han ;
Hollas, Daniel ;
Corminboeuf, Clemence .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2019, 21 (18) :9026-9035
[40]   A new fluorescent 'turn on' probe for rapid detection of biothiols [J].
Ucuncu, Muhammed ;
Zeybek, Huseyin ;
Karakus, Erman ;
Ucuncu, Canan ;
Emrullahoglu, Mustafa .
SUPRAMOLECULAR CHEMISTRY, 2020, 32 (12) :634-641