Synthesis and Optical Properties of Trioxatriangulenium Dyes with One and Two Peripheral Amino Substituents
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
Standard
Synthesis and Optical Properties of Trioxatriangulenium Dyes with One and Two Peripheral Amino Substituents. / Sørensen, Thomas Just; Laursen, Bo Wegge.
I: Journal of Organic Chemistry, Bind 75, Nr. 18, 2010, s. 6182–6190.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
Harvard
APA
Vancouver
Author
Bibtex
}
RIS
TY - JOUR
T1 - Synthesis and Optical Properties of Trioxatriangulenium Dyes with One and Two Peripheral Amino Substituents
AU - Sørensen, Thomas Just
AU - Laursen, Bo Wegge
PY - 2010
Y1 - 2010
N2 - Several derivatives of two new dye systems, with one or two dialkylamino donor groups attached to resonant positions at the periphery of a trioxatriangulenium ion, were synthesized. The mono- and bis-dialkylamino trioxatriangulenium salts (A1-TOTA+ and A2-TOTA+) were prepared from methoxy-substituted triphenylmethylium (TPM) compounds by aromatic nucleophilic substitution with secondary amines and subsequent intramolecular ring closure. The optical properties of the new triangulenium dyes and their TPM precursors were investigated and compared to those of known TPM and xanthenium dyes. The optical properties were found to be dependent on symmetry and charge localization in the conjugated framework. The trioxatriangulenium dye with two amino groups (A2-TOTA+) was found to be a strong fluorophore with properties as a blue-shifted rhodamine B. The mono-substituted compound (A1-TOTA+) was found to be only weakly fluorescent. We assign the weak fluorescence of A1-TOTA+ to an efficient but reversible formation of a nonfluorescent conformation in the excited state, favored by the large degree of charge localization in this dye with only one donor group. Udgivelsesdato: August 26
AB - Several derivatives of two new dye systems, with one or two dialkylamino donor groups attached to resonant positions at the periphery of a trioxatriangulenium ion, were synthesized. The mono- and bis-dialkylamino trioxatriangulenium salts (A1-TOTA+ and A2-TOTA+) were prepared from methoxy-substituted triphenylmethylium (TPM) compounds by aromatic nucleophilic substitution with secondary amines and subsequent intramolecular ring closure. The optical properties of the new triangulenium dyes and their TPM precursors were investigated and compared to those of known TPM and xanthenium dyes. The optical properties were found to be dependent on symmetry and charge localization in the conjugated framework. The trioxatriangulenium dye with two amino groups (A2-TOTA+) was found to be a strong fluorophore with properties as a blue-shifted rhodamine B. The mono-substituted compound (A1-TOTA+) was found to be only weakly fluorescent. We assign the weak fluorescence of A1-TOTA+ to an efficient but reversible formation of a nonfluorescent conformation in the excited state, favored by the large degree of charge localization in this dye with only one donor group. Udgivelsesdato: August 26
U2 - 10.1021/jo1009917
DO - 10.1021/jo1009917
M3 - Journal article
C2 - 20738142
VL - 75
SP - 6182
EP - 6190
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 18
ER -
ID: 21974700