A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction

被引:9
作者
Anderson, Christopher L. [1 ,2 ]
Liang, Jiatao [1 ,2 ]
Teat, Simon J. [3 ]
Garzon-Ruiz, Andres [4 ]
Nenon, David P. [2 ,5 ]
Navarro, Amparo [6 ]
Liu, Yi [1 ]
机构
[1] Lawrence Berkeley Natl Lab, Mol Foundry, One Cyclotron Rd, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[3] Lawrence Berkeley Natl Lab, Adv Light Source, One Cyclotron Rd, Berkeley, CA 94720 USA
[4] Univ Castilla La Mancha, Fac Pharm, Dept Phys Chem, Albacete 02071, Spain
[5] Lawrence Berkeley Natl Lab, Mat Sci Div, One Cyclotron Rd, Berkeley, CA 94720 USA
[6] Univ Jaen, Fac Expt Sci, Dept Phys & Analyt Chem, Jaen 23071, Spain
关键词
VAPOR-DEPOSITION; MACRO RINGS; CHEMISTRY; SPACE; BOND;
D O I
10.1039/d0cc00916d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The generation of a highly-substituted [2.2](2,5)pyrazinophane via a cascade reaction is presented. The pyrazinophane product is formed via the dimerization of a member of the para-azaquinodimethane (p-AQM) family of conjugated quinoidal compounds-reactivity that sheds light on the nature of stability in p-AQMs. Additionally, the electronic and structural nature of this highly-strained ring system are characterized.
引用
收藏
页码:4472 / 4475
页数:4
相关论文
共 24 条
[1]   Electronic Tuning of Mixed Quinoidal-Aromatic Conjugated Polyelectrolytes: Direct Ionic Substitution on Polymer Main-Chains [J].
Anderson, Christopher L. ;
Dai, Nan ;
Teat, Simon J. ;
He, Bo ;
Wang, Shu ;
Liu, Yi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (50) :17978-17985
[2]   Bichromophoric paracyclophanes: Models for interchromophore delocalization [J].
Bartholomew, GP ;
Bazan, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (01) :30-39
[3]   Stilbenoid dimers: Dissection of a paracyclophane chromophore [J].
Bazan, GC ;
Oldham, WJ ;
Lachicotte, RJ ;
Tretiak, S ;
Chernyak, V ;
Mukamel, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) :9188-9204
[4]   Discovery of a Class of Diketopiperazines as Antiprion Compounds [J].
Bolognesi, Maria Laura ;
Tran, Hoang Ngoc Ai ;
Staderini, Matteo ;
Monaco, Alessandro ;
Lopez-Cobenas, Alberto ;
Bongarzone, Salvatore ;
Biarnes, Xevi ;
Lopez-Alvarado, Pilar ;
Cabezas, Nieves ;
Caramelli, Maria ;
Carloni, Paolo ;
Carlos Menendez, J. ;
Legname, Giuseppe .
CHEMMEDCHEM, 2010, 5 (08) :1324-1334
[5]   CYCLOPHANE CHEMISTRY - BENT AND BATTERED BENZENE RINGS [J].
CRAM, DJ ;
CRAM, JM .
ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (06) :204-&
[6]   MACRO RINGS .20. TRANSANNULAR EFFECTS IN PI-PI-COMPLEXES [J].
CRAM, DJ ;
BAUER, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (22) :5971-5977
[7]   [2.2](2,6)PYRAZINOPHANES AND [2.2](2,5)PYRAZINOPHANES - SYNTHESIS AND MOLECULAR-STRUCTURE [J].
EIERMANN, U ;
KRIEGER, C ;
NEUGEBAUER, FA ;
STAAB, HA .
CHEMISCHE BERICHTE, 1990, 123 (03) :523-533
[8]   [2.2](2,5)PYRAZINOPHANES - SYNTHESIS AND MOLECULAR-STRUCTURE [J].
EIERMANN, U ;
KRIEGER, C ;
NEUGEBAUER, FA ;
STAAB, HA .
TETRAHEDRON LETTERS, 1988, 29 (30) :3655-3658
[9]   RADICAL IONS OF [2.2](2,5)PYRAZINOPHANES - AN ELECTRON-PARAMAGNETIC RESONANCE STUDY [J].
EIERMANN, U ;
NEUGEBAUER, FA ;
SYMONS, MCR ;
WYATT, JL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (01) :91-94
[10]   THE CHEMISTRY OF XYLYLENES .3. SOME REACTIONS OF RHO-XYLYLENE THAT OCCUR BY FREE RADICAL INTERMEDIATES [J].
ERREDE, LA ;
HOYT, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (02) :436-439