Syntheses and Properties of Tin-Containing Conjugated Heterocycles

被引:16
作者
Urrego-Riveros, Sara [1 ,2 ]
Ramirez y Medina, Isabel-Maria [1 ,2 ]
Hoffmann, Jonas [1 ,2 ]
Heitmann, Anne [1 ,2 ]
Staubitz, Anne [1 ,2 ]
机构
[1] Univ Bremen, Inst Organ & Analyt Chem, Leobener Str 7 NW2C, D-28359 Bremen, Germany
[2] Univ Bremen, MAPEX Ctr Mat & Proc, Bibliothekstr 1, D-28359 Bremen, Germany
关键词
aromaticity; heterocycles; optoelectronic properties; stannoles; tin; CROSS-COUPLING REACTIONS; POLYCYCLIC AROMATIC-HYDROCARBONS; EXCITED-STATE AROMATICITY; MAIN-GROUP ELEMENTS; GROUP-14; METALLOLES; OPTICAL-PROPERTIES; STANNOLE DIANION; ORGANIC-PHOTOCHEMISTRY; VALENCE ISOMERIZATION; METALLACYCLE TRANSFER;
D O I
10.1002/chem.201703533
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Heterocycles that contain tin atoms can be aromatic in a similar sense to well-known aromatic compounds such as benzene or thiophene, but such examples are rare. However, due to the low-lying sigma*-orbitals of the tin-substituent bond in stannoles, they are capable of sigma*-pi* conjugation in a way that is exclusive to heavier element containing heterocycles. This makes stannoles very interesting alternatives for purely organic heterocycles in material applications, in which optoelectronic properties are of interest. This Concept article will highlight the synthesis, reactivity and physical properties of stannoles and related fluorenostannoles. At first, a brief introduction to different types of tin-containing heterocycles is presented, followed by a discussion on different approaches to prepare stannoles, their reactivity and their physical properties. In addition, the first stannole-containing polymer will be reviewed.
引用
收藏
页码:5680 / 5696
页数:17
相关论文
共 111 条
[21]   BORA-AROMATIC SYSTEMS .8. THE PHYSICAL AND CHEMICAL CONSEQUENCES OF CYCLIC CONJUGATION IN BORACYCLOPOLYENES - THE ANTIAROMATIC CHARACTER OF PENTAARYLBOROLES [J].
EISCH, JJ ;
GALLE, JE ;
KOZIMA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) :379-385
[22]   METALLACYCLE TRANSFER FROM ZIRCONIUM TO MAIN-GROUP ELEMENTS - A VERSATILE SYNTHESIS OF HETEROCYCLES [J].
FAGAN, PJ ;
NUGENT, WA ;
CALABRESE, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :1880-1889
[23]   Perfluoropentaphenylborole [J].
Fan, Cheng ;
Piers, Warren E. ;
Parvez, Masood .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2955-2958
[24]   Electron delocalization and aromaticity in low-lying excited states of archetypal organic compounds [J].
Feixas, Ferran ;
Vandenbussche, Jelle ;
Bultinck, Patrick ;
Matito, Eduard ;
Sola, Miquel .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (46) :20690-20703
[25]   Electrochemical and photophysical properties of a series of group-14 metalloles [J].
Ferman, J ;
Kakareka, JP ;
Klooster, WT ;
Mullin, JL ;
Quattrucci, J ;
Ricci, JS ;
Tracy, HJ ;
Vining, WJ ;
Wallace, S .
INORGANIC CHEMISTRY, 1999, 38 (10) :2464-2472
[26]   Aromaticity in Group 14 Homologues of the Cyclopropenylium Cation [J].
Fernandez, Israel ;
Duvall, Matthew ;
Wu, Judy I-Chia ;
Schleyer, Paul von Rague ;
Frenking, Gernot .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (07) :2215-2224
[27]   Ring-current aromaticity in triplet states of 4n π electron monocycles [J].
Fowler, PW ;
Steiner, E ;
Jenneskens, LW .
CHEMICAL PHYSICS LETTERS, 2003, 371 (5-6) :719-723
[28]   Synthesis, self-assembly, and nonlinear optical properties of conjugated helical metal phthalocyanine derivatives [J].
Fox, JM ;
Katz, TJ ;
Van Elshocht, S ;
Verbiest, T ;
Kauranen, M ;
Persoons, A ;
Thongpanchang, T ;
Krauss, T ;
Brus, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (14) :3453-3459
[30]   2,7-Substituted Hexafluoroheterofluorenes as Potential Building Blocks for Electron Transporting Materials [J].
Geramita, Katharine ;
McBee, Jennifer ;
Tilley, T. Don .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) :820-829