Hydrogen-protected acenes

被引:24
作者
Athans, Andreas J. [1 ]
Briggs, Jonathan B. [1 ]
Jia, Wenling [1 ]
Miller, Glen P. [1 ]
机构
[1] Univ New Hampshire, Dept Chem, Durham, NH 03824 USA
基金
美国国家科学基金会;
关键词
D O I
10.1039/b700956a
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
The first systematic study concerning the hydrogenation of acenes and acene quinones is presented. Phenyl substituted acenes and acene quinones are hydrogenated in excellent yield and with complete regioselectivity using HI-AcOH. The resulting H-protected acenes bear alternating aromatic and non-aromatic rings and are stable, soluble molecules that may be stored indefinitely and then deprotected to afford the parent acenes. In this manner, H-protected acenes have been utilized in the syntheses of several [60] fullerene-acene adducts. Buckminsterfullerene also hydrogenates in HI-AcOH yielding C-3 nu symmetric C60H18.
引用
收藏
页码:2636 / 2641
页数:6
相关论文
共 49 条
[1]   Action of Grignard reagents on certain pentacenequinones, 6,13-diphenylpentacene [J].
Allen, CFH ;
Bell, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :1253-1260
[2]   ELECTRONIC-SPECTRA OF HEXACENE IN SOLUTION (GROUND-STATE, TRIPLET-STATE, DICATION AND DIANION) [J].
ANGLIKER, H ;
ROMMEL, E ;
WIRZ, J .
CHEMICAL PHYSICS LETTERS, 1982, 87 (02) :208-212
[3]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[4]   Oligoacenes: Theoretical prediction of open-shell singlet diradical ground states [J].
Bendikov, M ;
Duong, HM ;
Starkey, K ;
Houk, KN ;
Carter, EA ;
Wudl, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7416-7417
[5]   DIELS-ALDER REACTIVITY OF POLYCYCLIC AROMATIC-HYDROCARBONS .1. ACENES AND BENZOLOGS [J].
BIERMANN, D ;
SCHMIDT, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (09) :3163-3173
[6]   THE PHOTO-DIMERS OF ANTHRACENE, TETRACENE AND PENTACENE [J].
BIRKS, JB ;
APPLEYARD, JH ;
POPE, R .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1963, 2 (04) :493-495
[7]   THE PHOTOCHEMISTRY OF ANTHRACENES .3. INTER-RELATIONS BETWEEN FLUORESCENCE QUENCHING, DIMERIZATION, AND PHOTO-OXIDATION [J].
BOWEN, EJ ;
TANNER, DW .
TRANSACTIONS OF THE FARADAY SOCIETY, 1955, 51 (04) :475-481
[8]   ABINITIO EFFECTIVE HAMILTONIAN STUDY OF THE ELECTRONIC-PROPERTIES OF CONJUGATED POLYMERS [J].
BREDAS, JL ;
CHANCE, RR ;
BAUGHMAN, RH ;
SILBEY, R .
JOURNAL OF CHEMICAL PHYSICS, 1982, 76 (07) :3673-3678
[9]   Facile, scalable, regioselective synthesis of C3v C60H18 using organic polyamines [J].
Briggs, JB ;
Montgomery, M ;
Silva, LL ;
Miller, GP .
ORGANIC LETTERS, 2005, 7 (25) :5553-5555
[10]   [60]Fullerene-acene chemistry: a review [J].
Briggs, Jonathan B. ;
Miller, Glen P. .
COMPTES RENDUS CHIMIE, 2006, 9 (7-8) :916-927