Mixing Polyaromatic Scaffolds and Main Group Elements: Synthesis, Coordination and Optical Properties of Naphthyl-Fused Heteropines

被引:9
作者
Delouche, Thomas [1 ]
Roisnel, Thierry [1 ]
Dorcet, Vincent [1 ]
Hissler, Muriel [1 ]
Bouit, Pierre-Antoine [1 ]
机构
[1] Univ Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France
关键词
Fluorescence; Germanium; Heterocycles; Phosphorus; Pi-systems; WARPED NANOGRAPHENE; DERIVATIVES; REACTIVITY; COMPLEXES; ROUTE;
D O I
10.1002/ejic.202001097
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In this article, we describe the synthesis of polyaromatic heteropines including main group element (Phosphorus, Germanium) through Ni or Cu-mediated C-C coupling. Coordination complexes were synthesized with the sigma(3),lambda(3)-phosphepines using different metal ions (Au(I), Re(I), Pd(II)) showing that these P-heterocycles display the classical reactivity of two-electrons P-donor making them promising ligands. The optical properties were experimentally studied (UV-vis absorption and emission) and compared. Finally, both polyaromatic germepine and phosphepine appear as interesting building blocks for optoelectronics.
引用
收藏
页码:1082 / 1089
页数:8
相关论文
共 38 条
[21]   New advances in nanographene chemistry [J].
Narita, Akimitsu ;
Wang, Xiao-Ye ;
Feng, Xinliang ;
Muellen, Klaus .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (18) :6616-6643
[22]   Isomeric Dithienophosphepines: The Impact of Ring Fusion on Electronic and Structural Properties [J].
Padberg, Kevin ;
Ascherl, Johannes D. R. ;
Hampel, Frank ;
Kivala, Milan .
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (16) :3474-3478
[23]   Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications [J].
Parke, Sarah M. ;
Boone, Michael P. ;
Rivard, Eric .
CHEMICAL COMMUNICATIONS, 2016, 52 (61) :9485-9505
[24]   Phosphorus-olefin chelation in coordinated atropisomeric chiral auxiliaries [J].
Pregosin, Paul S. .
CHEMICAL COMMUNICATIONS, 2008, (40) :4875-4884
[25]   Synthesis of Blue-Luminescent Seven-Membered Phosphorus Heterocycles [J].
Regulska, Elzbieta ;
Ruppert, Heiko ;
Rominger, Frank ;
Romero-Nieto, Carlos .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02) :1247-1252
[26]   [d]-Carbon-carbon double bond engineering in diazaphosphepines: a pathway to modulate the chemical and electronic structures of heteropines [J].
Ren, Yi ;
Sezen, Melda ;
Guo, Fang ;
Jakle, Frieder ;
Loo, Yueh-Lin .
CHEMICAL SCIENCE, 2016, 7 (07) :4211-4219
[27]   Coordination Complexes of P-Containing Polycyclic Aromatic Hydrocarbons: Optical Properties and Solid-State Supramolecular Assembly [J].
Riobe, Francois ;
Szucs, Rozsa ;
Lescop, Christophe ;
Reau, Regis ;
Nyulaszi, Laszlo ;
Bouit, Pierre-Antoine ;
Hissler, Muriel .
ORGANOMETALLICS, 2017, 36 (14) :2502-2511
[28]   Tetrabenzo[8]circulene: Aromatic Saddles from Negatively Curved Graphene [J].
Sakamoto, Youichi ;
Suzuki, Toshiyasu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (38) :14074-14077
[29]   Synthesis and Redox Properties of Pyrrole- and Azulene-Fused Azacoronene [J].
Sasaki, Yoshiki ;
Takase, Masayoshi ;
Okujima, Tetsuo ;
Mori, Shigeki ;
Uno, Hidemitsu .
ORGANIC LETTERS, 2019, 21 (06) :1900-1903
[30]   Facile Route to Quadruply Annulated Borepins [J].
Schickedanz, Kai ;
Radtke, Julian ;
Bolte, Michael ;
Lerner, Hans-Wolfram ;
Wagner, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (07) :2842-2851