Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyes

Marco Santella; Eduardo Della Pia; Jakob Kryger Sørensen; Bo W. Laursen

doi:10.3762/bjoc.15.210

Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyes

Marco Santella, Eduardo Della Pia, Jakob Kryger Sørensen, Bo W. Laursen

2 Citations (Scopus)

Abstract

Triangulenium dyes functionalized with one, two or three ethylthiol functionalities were synthesized and their optical properties were studied. The sulfur functionalities were introduced by aromatic nucleophilic substitution of methoxy groups in triarylmethylium cations with ethanethiol followed by partial or full ring closure of the ortho positions with nitrogen or oxygen bridges leading to sulfur-functionalized acridinium, xanthenium or triangulenium dyes. For all the dye classes the sulfur functionalities are found to lead to intensely absorbing dyes in the visible range (470 to 515 nm), quite similar to known analogous dye systems with dialkylamino donor groups in place of the ethylthiol substituents. For the triangulenium derivatives significant fluorescence was observed (Φ_f = 0.1 to Φ_f = 0.3).

Original language	English
Journal	Beilstein Journal of Organic Chemistry
Volume	15
Pages (from-to)	2133-2141
ISSN	1860-5397
DOIs	https://doi.org/10.3762/bjoc.15.210
Publication status	Published - 9 Sept 2019

Keywords

acridinium dyes
aromatic nucleophilic substitution
fluorescent dyes
sulfur-functionalized dyes
triangulenium dyes
triarylmethylium

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10.3762/bjoc.15.210Licence: CC BY

Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyesFinal published version, 1.2 MBLicence: CC BY

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title = "Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyes",

abstract = "Triangulenium dyes functionalized with one, two or three ethylthiol functionalities were synthesized and their optical properties were studied. The sulfur functionalities were introduced by aromatic nucleophilic substitution of methoxy groups in triarylmethylium cations with ethanethiol followed by partial or full ring closure of the ortho positions with nitrogen or oxygen bridges leading to sulfur-functionalized acridinium, xanthenium or triangulenium dyes. For all the dye classes the sulfur functionalities are found to lead to intensely absorbing dyes in the visible range (470 to 515 nm), quite similar to known analogous dye systems with dialkylamino donor groups in place of the ethylthiol substituents. For the triangulenium derivatives significant fluorescence was observed (Φf = 0.1 to Φf = 0.3).",

keywords = "acridinium dyes, aromatic nucleophilic substitution, fluorescent dyes, sulfur-functionalized dyes, triangulenium dyes, triarylmethylium",

author = "Marco Santella and Pia, {Eduardo Della} and S{\o}rensen, {Jakob Kryger} and Laursen, {Bo W.}",

year = "2019",

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doi = "10.3762/bjoc.15.210",

language = "English",

volume = "15",

pages = "2133--2141",

journal = "Beilstein Journal of Organic Chemistry",

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TY - JOUR

T1 - Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyes

AU - Santella, Marco

AU - Pia, Eduardo Della

AU - Sørensen, Jakob Kryger

AU - Laursen, Bo W.

PY - 2019/9/9

Y1 - 2019/9/9

N2 - Triangulenium dyes functionalized with one, two or three ethylthiol functionalities were synthesized and their optical properties were studied. The sulfur functionalities were introduced by aromatic nucleophilic substitution of methoxy groups in triarylmethylium cations with ethanethiol followed by partial or full ring closure of the ortho positions with nitrogen or oxygen bridges leading to sulfur-functionalized acridinium, xanthenium or triangulenium dyes. For all the dye classes the sulfur functionalities are found to lead to intensely absorbing dyes in the visible range (470 to 515 nm), quite similar to known analogous dye systems with dialkylamino donor groups in place of the ethylthiol substituents. For the triangulenium derivatives significant fluorescence was observed (Φf = 0.1 to Φf = 0.3).

AB - Triangulenium dyes functionalized with one, two or three ethylthiol functionalities were synthesized and their optical properties were studied. The sulfur functionalities were introduced by aromatic nucleophilic substitution of methoxy groups in triarylmethylium cations with ethanethiol followed by partial or full ring closure of the ortho positions with nitrogen or oxygen bridges leading to sulfur-functionalized acridinium, xanthenium or triangulenium dyes. For all the dye classes the sulfur functionalities are found to lead to intensely absorbing dyes in the visible range (470 to 515 nm), quite similar to known analogous dye systems with dialkylamino donor groups in place of the ethylthiol substituents. For the triangulenium derivatives significant fluorescence was observed (Φf = 0.1 to Φf = 0.3).

KW - acridinium dyes

KW - aromatic nucleophilic substitution

KW - fluorescent dyes

KW - sulfur-functionalized dyes

KW - triangulenium dyes

KW - triarylmethylium

U2 - 10.3762/bjoc.15.210

DO - 10.3762/bjoc.15.210

M3 - Journal article

C2 - 31579076

SN - 2195-951X

VL - 15

SP - 2133

EP - 2141

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Synthesis and properties of sulfur-functionalized triarylmethylium, acridinium and triangulenium dyes

Abstract

Keywords

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