Extended Triangulenium Ions: Syntheses and Characterization of Benzo-Bridged Dioxa- and Diazatriangulenium Dyes

Martin Rosenberg; Marco Santella; Sidsel A. Bogh; Alberto Viñas Muñoz; Helene O. B. Andersen; Ole Hammerich; Ilkay Bora; Kasper Lincke; Bo W. Laursen

doi:10.1021/acs.joc.8b02978

Extended Triangulenium Ions: Syntheses and Characterization of Benzo-Bridged Dioxa- and Diazatriangulenium Dyes

Martin Rosenberg, Marco Santella, Sidsel A. Bogh, Alberto Viñas Muñoz, Helene O. B. Andersen, Ole Hammerich, Ilkay Bora, Kasper Lincke, Bo W. Laursen

9 Citations (Scopus)

Abstract

The very limited class of fluorophores, with a long fluorescence lifetime (>10 ns) and fluorescence beyond 550 nm, has been expanded with two benzo-fused triangulenium derivatives and two cationic [5]-helicene salts. The syntheses of the benzo-bridged dioxa- and diazatriangulenium derivatives (BDOTA⁺ and BDATA⁺, respectively) required two different synthetic approaches, which reflect the structural and physiochemical impact on the reactivity of [5]-helicenium precursors. Spectroscopic investigations show that the introduction of the benzo bridge into the triangulenium chromophore significantly redshifts the absorption and emission while maintaining fluorescence lifetimes above 10 ns. The combination of a high quantum yield, long fluorescence lifetime, and emission above 600 nm is possible only if the structural aspects of the triangulenium framework are perfectly harmonized to secure a low rate of nonradiative deactivation. The new benzo bridge may be a general motif to obtain red-shifted derivatives of other dye classes.

Original language	English
Journal	The Journal of Organic Chemistry
Volume	84
Issue number	5
Pages (from-to)	2556-2567
Number of pages	12
ISSN	0022-3263
DOIs	https://doi.org/10.1021/acs.joc.8b02978
Publication status	Published - Mar 2018

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title = "Extended Triangulenium Ions: Syntheses and Characterization of Benzo-Bridged Dioxa- and Diazatriangulenium Dyes",

abstract = "The very limited class of fluorophores, with a long fluorescence lifetime (>10 ns) and fluorescence beyond 550 nm, has been expanded with two benzo-fused triangulenium derivatives and two cationic [5]-helicene salts. The syntheses of the benzo-bridged dioxa- and diazatriangulenium derivatives (BDOTA+ and BDATA+, respectively) required two different synthetic approaches, which reflect the structural and physiochemical impact on the reactivity of [5]-helicenium precursors. Spectroscopic investigations show that the introduction of the benzo bridge into the triangulenium chromophore significantly redshifts the absorption and emission while maintaining fluorescence lifetimes above 10 ns. The combination of a high quantum yield, long fluorescence lifetime, and emission above 600 nm is possible only if the structural aspects of the triangulenium framework are perfectly harmonized to secure a low rate of nonradiative deactivation. The new benzo bridge may be a general motif to obtain red-shifted derivatives of other dye classes.",

author = "Martin Rosenberg and Marco Santella and Bogh, {Sidsel A.} and Mu{\~n}oz, {Alberto Vi{\~n}as} and Andersen, {Helene O. B.} and Ole Hammerich and Ilkay Bora and Kasper Lincke and Laursen, {Bo W.}",

year = "2018",

month = mar,

doi = "10.1021/acs.joc.8b02978",

language = "English",

volume = "84",

pages = "2556--2567",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Extended Triangulenium Ions

T2 - Syntheses and Characterization of Benzo-Bridged Dioxa- and Diazatriangulenium Dyes

AU - Rosenberg, Martin

AU - Santella, Marco

AU - Bogh, Sidsel A.

AU - Muñoz, Alberto Viñas

AU - Andersen, Helene O. B.

AU - Hammerich, Ole

AU - Bora, Ilkay

AU - Lincke, Kasper

AU - Laursen, Bo W.

PY - 2018/3

Y1 - 2018/3

N2 - The very limited class of fluorophores, with a long fluorescence lifetime (>10 ns) and fluorescence beyond 550 nm, has been expanded with two benzo-fused triangulenium derivatives and two cationic [5]-helicene salts. The syntheses of the benzo-bridged dioxa- and diazatriangulenium derivatives (BDOTA+ and BDATA+, respectively) required two different synthetic approaches, which reflect the structural and physiochemical impact on the reactivity of [5]-helicenium precursors. Spectroscopic investigations show that the introduction of the benzo bridge into the triangulenium chromophore significantly redshifts the absorption and emission while maintaining fluorescence lifetimes above 10 ns. The combination of a high quantum yield, long fluorescence lifetime, and emission above 600 nm is possible only if the structural aspects of the triangulenium framework are perfectly harmonized to secure a low rate of nonradiative deactivation. The new benzo bridge may be a general motif to obtain red-shifted derivatives of other dye classes.

AB - The very limited class of fluorophores, with a long fluorescence lifetime (>10 ns) and fluorescence beyond 550 nm, has been expanded with two benzo-fused triangulenium derivatives and two cationic [5]-helicene salts. The syntheses of the benzo-bridged dioxa- and diazatriangulenium derivatives (BDOTA+ and BDATA+, respectively) required two different synthetic approaches, which reflect the structural and physiochemical impact on the reactivity of [5]-helicenium precursors. Spectroscopic investigations show that the introduction of the benzo bridge into the triangulenium chromophore significantly redshifts the absorption and emission while maintaining fluorescence lifetimes above 10 ns. The combination of a high quantum yield, long fluorescence lifetime, and emission above 600 nm is possible only if the structural aspects of the triangulenium framework are perfectly harmonized to secure a low rate of nonradiative deactivation. The new benzo bridge may be a general motif to obtain red-shifted derivatives of other dye classes.

U2 - 10.1021/acs.joc.8b02978

DO - 10.1021/acs.joc.8b02978

M3 - Journal article

C2 - 30694674

SN - 0022-3263

VL - 84

SP - 2556

EP - 2567

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Extended Triangulenium Ions: Syntheses and Characterization of Benzo-Bridged Dioxa- and Diazatriangulenium Dyes

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