volume 58 issue 17 pages 11614-11621

Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom

Maodie Wang 1
Guanyu Zhang 1
P. Bobadova-Parvanova 2
Ashley N Merriweather 1
Lilian Odom 2
David Barbosa 2
Frank Fronczek 1
Kevin S. Smith 1
M. A. Vicente 1
Publication typeJournal Article
Publication date2019-08-20
scimago Q1
wos Q1
SJR0.958
CiteScore7.4
Impact factor4.7
ISSN00201669, 1520510X
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
An efficient synthesis of boron-functionalized cyclic BODIPY-Gly conjugates, using commercially available N-protected glycine amino acids and a BF2-BODIPY moiety as starting materials, is reported. The existence of two conformers (up and down) is revealed through comprehensive DFT calculations and 1H and 11B NMR analyses. The experimental and computational results indicate that all BODIPYs are stable in aqueous solutions at neutral pH and that Fmoc-BODIPY (4) is more stable than Ac-BODIPY (6) in the presence of trifluoroacetic acid (TFA). In part due to their enhanced rigidity, all BODIPY-Gly conjugates display increased fluorescence quantum yields (0.6 < Φ < 0.9) relative to the corresponding BF2-BODIPY, making them excellent candidates for fluorescence imaging applications.
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GOST |
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GOST Copy
Wang M. et al. Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom // Inorganic Chemistry. 2019. Vol. 58. No. 17. pp. 11614-11621.
GOST all authors (up to 50) Copy
Wang M., Zhang G., Bobadova-Parvanova P., Merriweather A. N., Odom L., Barbosa D., Fronczek F., Smith K. S., Vicente M. A. Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom // Inorganic Chemistry. 2019. Vol. 58. No. 17. pp. 11614-11621.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.inorgchem.9b01474
UR - https://doi.org/10.1021/acs.inorgchem.9b01474
TI - Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom
T2 - Inorganic Chemistry
AU - Wang, Maodie
AU - Zhang, Guanyu
AU - Bobadova-Parvanova, P.
AU - Merriweather, Ashley N
AU - Odom, Lilian
AU - Barbosa, David
AU - Fronczek, Frank
AU - Smith, Kevin S.
AU - Vicente, M. A.
PY - 2019
DA - 2019/08/20
PB - American Chemical Society (ACS)
SP - 11614-11621
IS - 17
VL - 58
PMID - 31430148
SN - 0020-1669
SN - 1520-510X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Wang,
author = {Maodie Wang and Guanyu Zhang and P. Bobadova-Parvanova and Ashley N Merriweather and Lilian Odom and David Barbosa and Frank Fronczek and Kevin S. Smith and M. A. Vicente},
title = {Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom},
journal = {Inorganic Chemistry},
year = {2019},
volume = {58},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.inorgchem.9b01474},
number = {17},
pages = {11614--11621},
doi = {10.1021/acs.inorgchem.9b01474}
}
MLA
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MLA Copy
Wang, Maodie, et al. “Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom.” Inorganic Chemistry, vol. 58, no. 17, Aug. 2019, pp. 11614-11621. https://doi.org/10.1021/acs.inorgchem.9b01474.