Photochemical double 5-exo cyclization of alkenyl-substituted dithienylacetylenes: Efficient synthesis of diarylated dithienofulvalenes

Aiko Fukazawa; Takashi Karasawa; Hongyu Zhang; Kazumitsu Minemura; Cristopher Camacho; Jian Wang; Stephan Irle; Shigehiro Yamaguchi

doi:10.1002/anie.201303738

Photochemical double 5-exo cyclization of alkenyl-substituted dithienylacetylenes: Efficient synthesis of diarylated dithienofulvalenes

Aiko Fukazawa, Takashi Karasawa, Hongyu Zhang, Kazumitsu Minemura, Cristopher Camacho, Jian Wang, Stephan Irle, Shigehiro Yamaguchi

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

13 Scopus citations

Abstract

Smooth and selective: Upon photoirradiation, bis(3-alkenyl-2-thienyl) acetylenes smoothly and selectively undergo double 5-exo-dig cyclization to produce a series of thiophene-fused pentafulvalenes with various aryl substituents. In this fused π-conjugated skeleton, the fused thiophene rings and the aryl substituents significantly modulate the electronic structure of the pentafulvalene skeleton.

Original language	English
Pages (from-to)	10519-10523
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	40
DOIs	https://doi.org/10.1002/anie.201303738
State	Published - Sep 27 2013
Externally published	Yes

Keywords

cyclization
pentafulvalene
photoreaction
redox properties
π conjugation

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10.1002/anie.201303738

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title = "Photochemical double 5-exo cyclization of alkenyl-substituted dithienylacetylenes: Efficient synthesis of diarylated dithienofulvalenes",

abstract = "Smooth and selective: Upon photoirradiation, bis(3-alkenyl-2-thienyl) acetylenes smoothly and selectively undergo double 5-exo-dig cyclization to produce a series of thiophene-fused pentafulvalenes with various aryl substituents. In this fused π-conjugated skeleton, the fused thiophene rings and the aryl substituents significantly modulate the electronic structure of the pentafulvalene skeleton.",

keywords = "cyclization, pentafulvalene, photoreaction, redox properties, π conjugation",

author = "Aiko Fukazawa and Takashi Karasawa and Hongyu Zhang and Kazumitsu Minemura and Cristopher Camacho and Jian Wang and Stephan Irle and Shigehiro Yamaguchi",

year = "2013",

month = sep,

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doi = "10.1002/anie.201303738",

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pages = "10519--10523",

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T1 - Photochemical double 5-exo cyclization of alkenyl-substituted dithienylacetylenes

T2 - Efficient synthesis of diarylated dithienofulvalenes

AU - Fukazawa, Aiko

AU - Karasawa, Takashi

AU - Zhang, Hongyu

AU - Minemura, Kazumitsu

AU - Camacho, Cristopher

AU - Wang, Jian

AU - Irle, Stephan

AU - Yamaguchi, Shigehiro

PY - 2013/9/27

Y1 - 2013/9/27

N2 - Smooth and selective: Upon photoirradiation, bis(3-alkenyl-2-thienyl) acetylenes smoothly and selectively undergo double 5-exo-dig cyclization to produce a series of thiophene-fused pentafulvalenes with various aryl substituents. In this fused π-conjugated skeleton, the fused thiophene rings and the aryl substituents significantly modulate the electronic structure of the pentafulvalene skeleton.

AB - Smooth and selective: Upon photoirradiation, bis(3-alkenyl-2-thienyl) acetylenes smoothly and selectively undergo double 5-exo-dig cyclization to produce a series of thiophene-fused pentafulvalenes with various aryl substituents. In this fused π-conjugated skeleton, the fused thiophene rings and the aryl substituents significantly modulate the electronic structure of the pentafulvalene skeleton.

KW - cyclization

KW - pentafulvalene

KW - photoreaction

KW - redox properties

KW - π conjugation

UR - https://www.scopus.com/pages/publications/84884844975

U2 - 10.1002/anie.201303738

DO - 10.1002/anie.201303738

M3 - Article

C2 - 23943526

AN - SCOPUS:84884844975

SN - 1433-7851

VL - 52

SP - 10519

EP - 10523

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 40

ER -

Photochemical double 5-exo cyclization of alkenyl-substituted dithienylacetylenes: Efficient synthesis of diarylated dithienofulvalenes

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Keywords

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