[n]Imperilenes: Stacked [n]trannulenes separated by planar cycloalkane rings

Farnaz A. Shakib; Mohammad R. Momeni; Judy I. Wu; Paul Von Ragué Schleyer; Zahra Azizi; Mehdi Ghambarian

doi:10.1021/ol201216d

[n]Imperilenes: Stacked [n]trannulenes separated by planar cycloalkane rings

Farnaz A. Shakib, Mohammad R. Momeni, Judy I. Wu, Paul Von Ragué Schleyer, Zahra Azizi, Mehdi Ghambarian

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

Two trannulene moieties fused to each other by means of perfectly planar cycloalkane rings comprise an interesting class of molecules (above) named "imperilenes". Based on computed geometries and NICS_zz values, only the [5], [7], and [9]imperilene singlet states as well as the 4+ charged [4], [6], and [8]imperilenes and their higher energy neutral quintet states are aromatic. The π electron systems of the individual trannulene rings, rather than the overall electron count, determine the behavior.

Original language	English (US)
Pages (from-to)	3600-3603
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	14
DOIs	https://doi.org/10.1021/ol201216d
State	Published - Jul 15 2011

Publisher link

10.1021/ol201216d

Find It

Find It at U of M Libraries

Cite this

@article{83d9b0d555244e7299cdeabea2712102,

title = "[n]Imperilenes: Stacked [n]trannulenes separated by planar cycloalkane rings",

abstract = "Two trannulene moieties fused to each other by means of perfectly planar cycloalkane rings comprise an interesting class of molecules (above) named {"}imperilenes{"}. Based on computed geometries and NICSzz values, only the [5], [7], and [9]imperilene singlet states as well as the 4+ charged [4], [6], and [8]imperilenes and their higher energy neutral quintet states are aromatic. The π electron systems of the individual trannulene rings, rather than the overall electron count, determine the behavior.",

author = "Shakib, {Farnaz A.} and Momeni, {Mohammad R.} and Wu, {Judy I.} and Schleyer, {Paul Von Ragu{\'e}} and Zahra Azizi and Mehdi Ghambarian",

year = "2011",

month = jul,

day = "15",

doi = "10.1021/ol201216d",

language = "English (US)",

volume = "13",

pages = "3600--3603",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - [n]Imperilenes

T2 - Stacked [n]trannulenes separated by planar cycloalkane rings

AU - Shakib, Farnaz A.

AU - Momeni, Mohammad R.

AU - Wu, Judy I.

AU - Schleyer, Paul Von Ragué

AU - Azizi, Zahra

AU - Ghambarian, Mehdi

PY - 2011/7/15

Y1 - 2011/7/15

N2 - Two trannulene moieties fused to each other by means of perfectly planar cycloalkane rings comprise an interesting class of molecules (above) named "imperilenes". Based on computed geometries and NICSzz values, only the [5], [7], and [9]imperilene singlet states as well as the 4+ charged [4], [6], and [8]imperilenes and their higher energy neutral quintet states are aromatic. The π electron systems of the individual trannulene rings, rather than the overall electron count, determine the behavior.

AB - Two trannulene moieties fused to each other by means of perfectly planar cycloalkane rings comprise an interesting class of molecules (above) named "imperilenes". Based on computed geometries and NICSzz values, only the [5], [7], and [9]imperilene singlet states as well as the 4+ charged [4], [6], and [8]imperilenes and their higher energy neutral quintet states are aromatic. The π electron systems of the individual trannulene rings, rather than the overall electron count, determine the behavior.

UR - http://www.scopus.com/inward/record.url?scp=79960167558&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79960167558&partnerID=8YFLogxK

U2 - 10.1021/ol201216d

DO - 10.1021/ol201216d

M3 - Article

C2 - 21667940

AN - SCOPUS:79960167558

SN - 1523-7060

VL - 13

SP - 3600

EP - 3603

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

[n]Imperilenes: Stacked [n]trannulenes separated by planar cycloalkane rings

Abstract

Publisher link

Find It

Other files and links

Fingerprint

Cite this