Benzo[e]pyrene skeleton dipyrylium dication with a strong donor-acceptor-donor interaction, and its two-electron reduced molecule

Koya Prabhakara Rao; Mio Kondo; Ryota Sakamoto; Tetsuro Kusamoto; Michihiro Nishikawa; Shoko Kume; Masayuki Nihei; Hiroki Oshio; Hiroshi Nishihara

doi:10.1002/chem.201101708

Benzo[e]pyrene skeleton dipyrylium dication with a strong donor-acceptor-donor interaction, and its two-electron reduced molecule

Koya Prabhakara Rao, Mio Kondo, Ryota Sakamoto, Tetsuro Kusamoto, Michihiro Nishikawa, Shoko Kume, Masayuki Nihei, Hiroki Oshio, Hiroshi Nishihara

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

21 Citations (Scopus)

Abstract

The donor-acceptor-donor (D-A-D) conjugated molecules 1,4- bis(diarylaminophenylethynyl)anthraquinone (1,4-Am₂Aq) and 1,4-bis(ferrocenylethynyl)anthraquinone (1,4-Fc₂Aq), undergo a double proton cyclization reaction with bis(trifluoromethanesulfone)imide acid (TFSIH) to yield 1,4-bis(diarylaminophenyl or ferrocenyl) dipyrylium salts [1,4-R ₂Pyl₂](TFSI)₂ (R=Am or Fc) with novel planar pentacyclic structures similar to the aromatic benzo[e]pyrene-type skeleton. [1,4-Am₂Pyl₂](TFSI)₂ could be reduced to give the neutral molecule [1,4-Am₂Pyl₂]⁰, which is stable and maintains the benzo[e]pyrene-type skeleton.

Original language	English
Pages (from-to)	14010-14019
Number of pages	10
Journal	Chemistry - A European Journal
Volume	17
Issue number	50
DOIs	https://doi.org/10.1002/chem.201101708
Publication status	Published - 2011 Dec 9
Externally published	Yes

Keywords

donor-acceptor systems
pi interactions
protonation-induced cyclization
redox chemistry
valence tautomerization

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201101708

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title = "Benzo[e]pyrene skeleton dipyrylium dication with a strong donor-acceptor-donor interaction, and its two-electron reduced molecule",

abstract = "The donor-acceptor-donor (D-A-D) conjugated molecules 1,4- bis(diarylaminophenylethynyl)anthraquinone (1,4-Am2Aq) and 1,4-bis(ferrocenylethynyl)anthraquinone (1,4-Fc2Aq), undergo a double proton cyclization reaction with bis(trifluoromethanesulfone)imide acid (TFSIH) to yield 1,4-bis(diarylaminophenyl or ferrocenyl) dipyrylium salts [1,4-R 2Pyl2](TFSI)2 (R=Am or Fc) with novel planar pentacyclic structures similar to the aromatic benzo[e]pyrene-type skeleton. [1,4-Am2Pyl2](TFSI)2 could be reduced to give the neutral molecule [1,4-Am2Pyl2]0, which is stable and maintains the benzo[e]pyrene-type skeleton.",

keywords = "donor-acceptor systems, pi interactions, protonation-induced cyclization, redox chemistry, valence tautomerization",

author = "Rao, {Koya Prabhakara} and Mio Kondo and Ryota Sakamoto and Tetsuro Kusamoto and Michihiro Nishikawa and Shoko Kume and Masayuki Nihei and Hiroki Oshio and Hiroshi Nishihara",

year = "2011",

month = dec,

day = "9",

doi = "10.1002/chem.201101708",

language = "English",

volume = "17",

pages = "14010--14019",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

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TY - JOUR

T1 - Benzo[e]pyrene skeleton dipyrylium dication with a strong donor-acceptor-donor interaction, and its two-electron reduced molecule

AU - Rao, Koya Prabhakara

AU - Kondo, Mio

AU - Sakamoto, Ryota

AU - Kusamoto, Tetsuro

AU - Nishikawa, Michihiro

AU - Kume, Shoko

AU - Nihei, Masayuki

AU - Oshio, Hiroki

AU - Nishihara, Hiroshi

PY - 2011/12/9

Y1 - 2011/12/9

N2 - The donor-acceptor-donor (D-A-D) conjugated molecules 1,4- bis(diarylaminophenylethynyl)anthraquinone (1,4-Am2Aq) and 1,4-bis(ferrocenylethynyl)anthraquinone (1,4-Fc2Aq), undergo a double proton cyclization reaction with bis(trifluoromethanesulfone)imide acid (TFSIH) to yield 1,4-bis(diarylaminophenyl or ferrocenyl) dipyrylium salts [1,4-R 2Pyl2](TFSI)2 (R=Am or Fc) with novel planar pentacyclic structures similar to the aromatic benzo[e]pyrene-type skeleton. [1,4-Am2Pyl2](TFSI)2 could be reduced to give the neutral molecule [1,4-Am2Pyl2]0, which is stable and maintains the benzo[e]pyrene-type skeleton.

AB - The donor-acceptor-donor (D-A-D) conjugated molecules 1,4- bis(diarylaminophenylethynyl)anthraquinone (1,4-Am2Aq) and 1,4-bis(ferrocenylethynyl)anthraquinone (1,4-Fc2Aq), undergo a double proton cyclization reaction with bis(trifluoromethanesulfone)imide acid (TFSIH) to yield 1,4-bis(diarylaminophenyl or ferrocenyl) dipyrylium salts [1,4-R 2Pyl2](TFSI)2 (R=Am or Fc) with novel planar pentacyclic structures similar to the aromatic benzo[e]pyrene-type skeleton. [1,4-Am2Pyl2](TFSI)2 could be reduced to give the neutral molecule [1,4-Am2Pyl2]0, which is stable and maintains the benzo[e]pyrene-type skeleton.

KW - donor-acceptor systems

KW - pi interactions

KW - protonation-induced cyclization

KW - redox chemistry

KW - valence tautomerization

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DO - 10.1002/chem.201101708

M3 - Article

AN - SCOPUS:82155182073

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 50

ER -

Benzo[e]pyrene skeleton dipyrylium dication with a strong donor-acceptor-donor interaction, and its two-electron reduced molecule

Abstract

Keywords

ASJC Scopus subject areas

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