Synthesis, Properties, and Design Principles of Donor-Acceptor Nanohoops

被引：125

作者：

Darzi, Evan R. ^{[1
]}

Hirst, Elizabeth S. ^{[1
]}

Weber, Christopher D. ^{[1
]}

Zakharov, Lev N. ^{[1
]}

Lonergan, Mark C. ^{[1
]}

Jasti, Ramesh ^{[1
]}

机构：

[1] Univ Oregon, Dept Chem & Biochem, Eugene, OR 97403 USA

来源：

ACS CENTRAL SCIENCE | 2015年 / 1卷 / 06期

基金：

美国国家科学基金会;

关键词：

PHOTOPHYSICAL PROPERTIES; ELECTRONIC-PROPERTIES; CARBON NANOTUBES; BEARING;

D O I：

10.1021/acscentsci.5b00269

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have synthesized a series of aza[8]cyclo-paraphenylenes containing one, two, and three nitrogens to probe the impact of nitrogen doping on optoelectronic properties and solid state packing. Alkylation of these azananohoops afforded the first donor-acceptor nanohoops where the phenylene backbone acts as the donor and the pyridinium units act as the acceptor. The impact on the optoelectronic properties was then studied experimentally and computationally to provide new insight into the effect of functionalization on nanohoops properties.

引用

页码：335 / 342

页数：8

共 44 条

[1] Self-Trapping of Excitons, Violation of Condon Approximation, and Efficient Fluorescence in Conjugated Cycloparaphenylenes [J].

Adamska, Lyudmyla ;

Nayyar, Iffat ;

Chen, Hang ;

Swan, Anna K. ;

Oldani, Nicolas ;

Fernandez-Alberti, Sebastian ;

Golder, Matthew R. ;

Jasti, Ramesh ;

Doorn, Stephen K. ;

Tretiak, Sergei .

NANO LETTERS, 2014, 14 (11) :6539-6546

[2] Functionalized acenes and heteroacenes for organic electronics [J].

Anthony, John E. .

CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048

[3] DFT Study of Cycloparaphenylenes and Heteroatom-Substituted Nanohoops [J].

Bachrach, Steven M. ;

Stueck, David .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (19) :6595-6604

[4] Chiral Conjugated Corrals [J].

Ball, Melissa ;

Fowler, Brandon ;

Li, Panpan ;

Joyce, Leo A. ;

Li, Fang ;

Liu, Taifeng ;

Paley, Daniel ;

Zhong, Yu ;

Li, Hexing ;

Xiao, Shengxiong ;

Ng, Fay ;

Steigerwald, Michael L. ;

Nuckolls, Colin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (31) :9982-9987

[5] Synthesis of Nitrogen-Doped ZigZag-Edge Peripheries: Dibenzo-9a-azaphenalene as Repeating Unit [J].

Berger, Reinhard ;

Giannakopoulos, Angelos ;

Ravat, Prince ;

Wagner, Manfred ;

Beljonne, David ;

Feng, Xinliang ;

Muellen, Klaus .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (39) :10520-10524

[6] Organic semiconductors:: A theoretical characterization of the basic parameters governing charge transport [J].

Brédas, JL ;

Calbert, JP ;

da Silva, DA ;

Cornil, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (09) :5804-5809

[7] INFLUENCE OF DONOR AND ACCEPTOR SUBSTITUENTS ON THE ELECTRONIC CHARACTERISTICS OF POLY(PARA-PHENYLENE VINYLENE) AND POLY(PARA-PHENYLENE) [J].

BREDAS, JL ;

HEEGER, AJ .

CHEMICAL PHYSICS LETTERS, 1994, 217 (5-6) :507-512

[8] A study of the lithiation of 2,6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010 [J].

Cai, DW ;

Hughes, DL ;

Verhoeven, TR .

TETRAHEDRON LETTERS, 1996, 37 (15) :2537-2540

[9] The structural and electronic promoting effect of nitrogen-doped carbon nanotubes on supported Pd nanoparticles for selective olefin hydrogenation [J].

Chen, Peirong ;

Chew, Ly May ;

Kostka, Aleksander ;

Muhler, Martin ;

Xia, Wei .

CATALYSIS SCIENCE & TECHNOLOGY, 2013, 3 (08) :1964-1971

[10] The dynamic, size-dependent properties of [5]-[12]cycloparaphenylenes [J].

Darzi, Evan R. ;

Jasti, Ramesh .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (18) :6401-6410

← 1 2 3 4 5 →