Linearly Polymerized Benzene Arrays As Intermediates, Tracing Pathways to Carbon Nanothreads

Bo Chen, Roald Hoffmann, N. W. Ashcroft, John Badding, Enshi Xu, Vincent Crespi

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

How might fully saturated benzene polymers of composition [(CH)6]n form under high pressure? In the first approach to answering this question, we examine the stepwise increase in saturation of a one-dimensional stack of benzene molecules by enumerating the partially saturated polymer intermediates, subject to constraints of unit cell size and energy. Defining the number of four-coordinate carbon atoms per benzene formula unit as the degree of saturation, a set of isomers for degree-two and degree-four polymers can be generated by either thinking of the propagation of partially saturated building blocks or by considering a sequence of cycloadditions. There is also one 4 + 2 reaction sequence that jumps directly from a benzene stack to a degree-four polymer. The set of degree-two polymers provides several useful signposts toward achieving full saturation: chiral versus achiral building blocks, certain forms of conformational freedom, and also dead ends to further saturation. These insights allow us to generate a larger set of degree-four polymers and enumerate the many pathways that lead from benzene stacks to completely saturated carbon nanothreads.

Original languageEnglish (US)
Pages (from-to)14373-14386
Number of pages14
JournalJournal of the American Chemical Society
Volume137
Issue number45
DOIs
StatePublished - Oct 21 2015

Fingerprint

Benzene
Polymers
Carbon
Cycloaddition
Cycloaddition Reaction
Cell Size
Isomers
Pressure
Atoms
Molecules
Chemical analysis

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Chen, Bo ; Hoffmann, Roald ; Ashcroft, N. W. ; Badding, John ; Xu, Enshi ; Crespi, Vincent. / Linearly Polymerized Benzene Arrays As Intermediates, Tracing Pathways to Carbon Nanothreads. In: Journal of the American Chemical Society. 2015 ; Vol. 137, No. 45. pp. 14373-14386.
@article{3dbc5f7b169e46c58c1cb32d1c4b92ff,
title = "Linearly Polymerized Benzene Arrays As Intermediates, Tracing Pathways to Carbon Nanothreads",
abstract = "How might fully saturated benzene polymers of composition [(CH)6]n form under high pressure? In the first approach to answering this question, we examine the stepwise increase in saturation of a one-dimensional stack of benzene molecules by enumerating the partially saturated polymer intermediates, subject to constraints of unit cell size and energy. Defining the number of four-coordinate carbon atoms per benzene formula unit as the degree of saturation, a set of isomers for degree-two and degree-four polymers can be generated by either thinking of the propagation of partially saturated building blocks or by considering a sequence of cycloadditions. There is also one 4 + 2 reaction sequence that jumps directly from a benzene stack to a degree-four polymer. The set of degree-two polymers provides several useful signposts toward achieving full saturation: chiral versus achiral building blocks, certain forms of conformational freedom, and also dead ends to further saturation. These insights allow us to generate a larger set of degree-four polymers and enumerate the many pathways that lead from benzene stacks to completely saturated carbon nanothreads.",
author = "Bo Chen and Roald Hoffmann and Ashcroft, {N. W.} and John Badding and Enshi Xu and Vincent Crespi",
year = "2015",
month = "10",
day = "21",
doi = "10.1021/jacs.5b09053",
language = "English (US)",
volume = "137",
pages = "14373--14386",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "45",

}

Linearly Polymerized Benzene Arrays As Intermediates, Tracing Pathways to Carbon Nanothreads. / Chen, Bo; Hoffmann, Roald; Ashcroft, N. W.; Badding, John; Xu, Enshi; Crespi, Vincent.

In: Journal of the American Chemical Society, Vol. 137, No. 45, 21.10.2015, p. 14373-14386.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Linearly Polymerized Benzene Arrays As Intermediates, Tracing Pathways to Carbon Nanothreads

AU - Chen, Bo

AU - Hoffmann, Roald

AU - Ashcroft, N. W.

AU - Badding, John

AU - Xu, Enshi

AU - Crespi, Vincent

PY - 2015/10/21

Y1 - 2015/10/21

N2 - How might fully saturated benzene polymers of composition [(CH)6]n form under high pressure? In the first approach to answering this question, we examine the stepwise increase in saturation of a one-dimensional stack of benzene molecules by enumerating the partially saturated polymer intermediates, subject to constraints of unit cell size and energy. Defining the number of four-coordinate carbon atoms per benzene formula unit as the degree of saturation, a set of isomers for degree-two and degree-four polymers can be generated by either thinking of the propagation of partially saturated building blocks or by considering a sequence of cycloadditions. There is also one 4 + 2 reaction sequence that jumps directly from a benzene stack to a degree-four polymer. The set of degree-two polymers provides several useful signposts toward achieving full saturation: chiral versus achiral building blocks, certain forms of conformational freedom, and also dead ends to further saturation. These insights allow us to generate a larger set of degree-four polymers and enumerate the many pathways that lead from benzene stacks to completely saturated carbon nanothreads.

AB - How might fully saturated benzene polymers of composition [(CH)6]n form under high pressure? In the first approach to answering this question, we examine the stepwise increase in saturation of a one-dimensional stack of benzene molecules by enumerating the partially saturated polymer intermediates, subject to constraints of unit cell size and energy. Defining the number of four-coordinate carbon atoms per benzene formula unit as the degree of saturation, a set of isomers for degree-two and degree-four polymers can be generated by either thinking of the propagation of partially saturated building blocks or by considering a sequence of cycloadditions. There is also one 4 + 2 reaction sequence that jumps directly from a benzene stack to a degree-four polymer. The set of degree-two polymers provides several useful signposts toward achieving full saturation: chiral versus achiral building blocks, certain forms of conformational freedom, and also dead ends to further saturation. These insights allow us to generate a larger set of degree-four polymers and enumerate the many pathways that lead from benzene stacks to completely saturated carbon nanothreads.

UR - http://www.scopus.com/inward/record.url?scp=84947998607&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84947998607&partnerID=8YFLogxK

U2 - 10.1021/jacs.5b09053

DO - 10.1021/jacs.5b09053

M3 - Article

C2 - 26488180

AN - SCOPUS:84947998607

VL - 137

SP - 14373

EP - 14386

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 45

ER -