A General Synthetic Route to 3,5-Substituted Boron Dipyrromethenes: Applications and Properties
1
Laboratoire
de Chimie Organique et Spectroscopies Avancées
(LCOSA), ECPM, UMR 7515, CNRS-UDS, 25 rue
Becquerel, 67087 Strasbourg Cedex 02, France
|
Publication type: Journal Article
Publication date: 2012-04-23
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
22497543
Organic Chemistry
Abstract
An efficient protocol for the direct synthesis of 3-substituted and 3,5-disubstituted BODIPY derivatives via electrophilic attack with NBS was developed. Various substituents like ethers, sugar, hydroxyl, thiophene, sulfur, azide, tertiary amines, alkyne, vinyl, or phosphonate groups were obtained in moderate to excellent yields. The amine-substituted derivatives display unusual spectroscopic and electrochemical properties which were analyzed in solution in the presence of HCl. The diethylamino-substituted derivative has a proton association constant of log β = 4.7, and the disubstituted derivative has two association constants of log β = 6.2 and 12.1 in ethanol. In both cases, the quenching of the fluorescence is explained by photoinduced electron transfer from the tertiary amine to the Bodipy excited state.
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43
Total citations:
43
Citations from 2024:
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(11.63%)
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GOST
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Ulrich G., Ziessel R., Haefele A. A General Synthetic Route to 3,5-Substituted Boron Dipyrromethenes: Applications and Properties // Journal of Organic Chemistry. 2012. Vol. 77. No. 9. pp. 4298-4311.
GOST all authors (up to 50)
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Ulrich G., Ziessel R., Haefele A. A General Synthetic Route to 3,5-Substituted Boron Dipyrromethenes: Applications and Properties // Journal of Organic Chemistry. 2012. Vol. 77. No. 9. pp. 4298-4311.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo3002408
UR - https://doi.org/10.1021/jo3002408
TI - A General Synthetic Route to 3,5-Substituted Boron Dipyrromethenes: Applications and Properties
T2 - Journal of Organic Chemistry
AU - Ulrich, G.
AU - Ziessel, Raymond
AU - Haefele, Alexandre
PY - 2012
DA - 2012/04/23
PB - American Chemical Society (ACS)
SP - 4298-4311
IS - 9
VL - 77
PMID - 22497543
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2012_Ulrich,
author = {G. Ulrich and Raymond Ziessel and Alexandre Haefele},
title = {A General Synthetic Route to 3,5-Substituted Boron Dipyrromethenes: Applications and Properties},
journal = {Journal of Organic Chemistry},
year = {2012},
volume = {77},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/jo3002408},
number = {9},
pages = {4298--4311},
doi = {10.1021/jo3002408}
}
Cite this
MLA
Copy
Ulrich, G., et al. “A General Synthetic Route to 3,5-Substituted Boron Dipyrromethenes: Applications and Properties.” Journal of Organic Chemistry, vol. 77, no. 9, Apr. 2012, pp. 4298-4311. https://doi.org/10.1021/jo3002408.