Quadrupolar, emission-tunable pi-expanded 1,4-dihydropyrrolo 3,2-b pyrroles - synthesis and optical properties

A. Janiga, D. Bednarska, B. Thorsted, J. Brewer, D. T. Gryko

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

The synthesis and optical characterization of six novel heteroaromatic-based chromophores is described. The new dyes present mostly an A-D-A general framework, where A is an electron-deficient aromatic ring and D is an electron-rich pyrrolo[3,2-b] pyrrole moiety, linked via triple bonds. It was demonstrated that the increase in the molecular length of the chromophore effectively extends pi-conjugation. The effect of structural variations on photophysical properties was studied in detail for these compounds and the relationship between the structure and photophysical properties was thoroughly elucidated by comparison with simpler tetraaryl-analogues. The strong charge-transfer characteristic of these functional dyes can be illustrated by large Stokes shifts (4100-7100 cm(-1)) for A-D-A architectures. The replacement of phenyl rings at positions 2 and 5 with the arylethynylaryl substituents bathochromically shifts both absorption and emission at ca. 50-150 nm. The clear dependence of fluorescence maxima on the electron-accepting property of the peripheral arylethynyl substituent emphasizes strong p-conjugation in these molecules. The donor-acceptor interactions were also found to influence the two-photon absorption properties.
OriginalsprogEngelsk
TidsskriftOrganic & Biomolecular Chemistry
Vol/bind12
Udgave nummer18
Sider (fra-til)2874-2881
ISSN1477-0520
DOI
StatusUdgivet - 2014

Citer dette

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title = "Quadrupolar, emission-tunable pi-expanded 1,4-dihydropyrrolo 3,2-b pyrroles - synthesis and optical properties",
abstract = "The synthesis and optical characterization of six novel heteroaromatic-based chromophores is described. The new dyes present mostly an A-D-A general framework, where A is an electron-deficient aromatic ring and D is an electron-rich pyrrolo[3,2-b] pyrrole moiety, linked via triple bonds. It was demonstrated that the increase in the molecular length of the chromophore effectively extends pi-conjugation. The effect of structural variations on photophysical properties was studied in detail for these compounds and the relationship between the structure and photophysical properties was thoroughly elucidated by comparison with simpler tetraaryl-analogues. The strong charge-transfer characteristic of these functional dyes can be illustrated by large Stokes shifts (4100-7100 cm(-1)) for A-D-A architectures. The replacement of phenyl rings at positions 2 and 5 with the arylethynylaryl substituents bathochromically shifts both absorption and emission at ca. 50-150 nm. The clear dependence of fluorescence maxima on the electron-accepting property of the peripheral arylethynyl substituent emphasizes strong p-conjugation in these molecules. The donor-acceptor interactions were also found to influence the two-photon absorption properties.",
author = "A. Janiga and D. Bednarska and B. Thorsted and J. Brewer and Gryko, {D. T.}",
year = "2014",
doi = "10.1039/c4ob00143e",
language = "English",
volume = "12",
pages = "2874--2881",
journal = "Organic & Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "18",

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Quadrupolar, emission-tunable pi-expanded 1,4-dihydropyrrolo 3,2-b pyrroles - synthesis and optical properties. / Janiga, A.; Bednarska, D.; Thorsted, B.; Brewer, J.; Gryko, D. T.

I: Organic & Biomolecular Chemistry, Bind 12, Nr. 18, 2014, s. 2874-2881.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Quadrupolar, emission-tunable pi-expanded 1,4-dihydropyrrolo 3,2-b pyrroles - synthesis and optical properties

AU - Janiga, A.

AU - Bednarska, D.

AU - Thorsted, B.

AU - Brewer, J.

AU - Gryko, D. T.

PY - 2014

Y1 - 2014

N2 - The synthesis and optical characterization of six novel heteroaromatic-based chromophores is described. The new dyes present mostly an A-D-A general framework, where A is an electron-deficient aromatic ring and D is an electron-rich pyrrolo[3,2-b] pyrrole moiety, linked via triple bonds. It was demonstrated that the increase in the molecular length of the chromophore effectively extends pi-conjugation. The effect of structural variations on photophysical properties was studied in detail for these compounds and the relationship between the structure and photophysical properties was thoroughly elucidated by comparison with simpler tetraaryl-analogues. The strong charge-transfer characteristic of these functional dyes can be illustrated by large Stokes shifts (4100-7100 cm(-1)) for A-D-A architectures. The replacement of phenyl rings at positions 2 and 5 with the arylethynylaryl substituents bathochromically shifts both absorption and emission at ca. 50-150 nm. The clear dependence of fluorescence maxima on the electron-accepting property of the peripheral arylethynyl substituent emphasizes strong p-conjugation in these molecules. The donor-acceptor interactions were also found to influence the two-photon absorption properties.

AB - The synthesis and optical characterization of six novel heteroaromatic-based chromophores is described. The new dyes present mostly an A-D-A general framework, where A is an electron-deficient aromatic ring and D is an electron-rich pyrrolo[3,2-b] pyrrole moiety, linked via triple bonds. It was demonstrated that the increase in the molecular length of the chromophore effectively extends pi-conjugation. The effect of structural variations on photophysical properties was studied in detail for these compounds and the relationship between the structure and photophysical properties was thoroughly elucidated by comparison with simpler tetraaryl-analogues. The strong charge-transfer characteristic of these functional dyes can be illustrated by large Stokes shifts (4100-7100 cm(-1)) for A-D-A architectures. The replacement of phenyl rings at positions 2 and 5 with the arylethynylaryl substituents bathochromically shifts both absorption and emission at ca. 50-150 nm. The clear dependence of fluorescence maxima on the electron-accepting property of the peripheral arylethynyl substituent emphasizes strong p-conjugation in these molecules. The donor-acceptor interactions were also found to influence the two-photon absorption properties.

U2 - 10.1039/c4ob00143e

DO - 10.1039/c4ob00143e

M3 - Journal article

VL - 12

SP - 2874

EP - 2881

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

IS - 18

ER -