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Bicyclic Baird-type aromaticity

Title
Bicyclic Baird-type aromaticity
Authors
Cha, Won-YoungKim, TaeyeonGhosh, ArindamZhang, ZhanKe, Xian-ShengAli, RashidLynch, Vincent M.Jung, JieunKim, WoojaeLee, SangsuFukuzumi, ShunichiPark, Jung SuSessler, Jonathan L.Chandrashekar, Tavarekere K.Kim, Dongho
Ewha Authors
Shunichi Fukuzumi
SCOPUS Author ID
Shunichi Fukuzumiscopus
Issue Date
2017
Journal Title
NATURE CHEMISTRY
ISSN
1755-4330JCR Link1755-4349JCR Link
Citation
vol. 9, no. 12, pp. 1243 - 1248
Publisher
NATURE PUBLISHING GROUP
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Classic formulations of aromaticity have long been associated with topologically planar conjugated macrocyclic systems. The theoretical possibility of so-called bicycloaromaticity was noted early on. However, it has yet to be demonstrated by experiment in a simple synthetic organic molecule. Conjugated organic systems are attractive for studying the effect of structure on electronic features. This is because, in principle, they can be modified readily through dedicated synthesis. As such, they can provide useful frameworks for testing by experiment with fundamental insights provided by theory. Here we detail the synthesis and characterization of two purely organic non-planar dithienothiophene-bridged [ 34] octaphyrins that permit access to two different aromatic forms as a function of the oxidation state. In their neutral forms, these congeneric systems contain competing 26 and 34 pi-electronic circuits. When subject to two-electron oxidation, electronically mixed [4n+1]/[4n+1] triplet biradical species in the ground state are obtained that display global aromaticity in accord with Baird's rule.
DOI
10.1038/NCHEM.2834
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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