Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure-properties relationship

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F16%3A00467663" target="_blank" >RIV/68378271:_____/16:00467663 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.tet.2016.09.063" target="_blank" >http://dx.doi.org/10.1016/j.tet.2016.09.063</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2016.09.063" target="_blank" >10.1016/j.tet.2016.09.063</a>

Result language

angličtina

Original language name

Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure-properties relationship

Original language description

We devised and synthesized a series of electron-rich compounds featuring diphenylamine, carbazole or dibenzo[c,g]carbazole connected via phenylacetylene linkers to an aromatic central unit. The key synthetic step was a high yielding cross coupling reaction between halogenated (bi)naphthalene and organometallic reagents prepared in situ from terminal alkynes (side-arms). By masking one of the iodo functions with a diethyltriazenyl group in the side-arm precursors, we efficiently circumvented the formation of doubly aminated by-products. Although one step longer, this approach led to higher yields of terminal alkynes than the direct coupling route. Spectroscopic and electrochemical measurementsnsupported by computational evidence revealed that conjugation in the 1,4-disubstituted naphthalene backbone is superior to the 1,5 or 2,6 substituted cores.n

Czech name

—

Czech description

—

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

BM - Solid-state physics and magnetism

OECD FORD branch

—

Project

<a href="/en/project/GA14-03276S" target="_blank" >GA14-03276S: Aspherical effects and their application for statistically correct crystal structure analysis</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Tetrahedron

ISSN

0040-4020

e-ISSN

—

Volume of the periodical

72

Issue of the periodical within the volume

44

Country of publishing house

GB - UNITED KINGDOM

Number of pages

12

Pages from-to

7081-7092

UT code for WoS article

000386404600025

EID of the result in the Scopus database

2-s2.0-84990853612