Journal of Organic Chemistry, volume 77, issue 10, pages 4516-4527
Heavy Atom Free Singlet Oxygen Generation: Doubly Substituted Configurations Dominate S1 States of Bis-BODIPYs
Publication type: Journal Article
Publication date: 2012-05-02
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
S(0), S(1), and T(1) states of various orthogonal 8,8' and 8,2'-bis-boradiaza-s-indacene (BODIPY) dyes, recently (Angew. Chem., Int. Ed.2011, 50, 11937) proposed as heavy atom free photosensitizers for O(2)((1)Δ(g)) generation, were studied by multireference quantum chemical approaches. S(0)→S(1) excitation characteristics of certain bis-BODIPYs are shown to be drastically different than the parent BODIPY chromophore. Whereas a simple HOMO→LUMO-type single substitution perfectly accounts for the BODIPY core, S(1) states of certain orthogonal bis-BODIPYs are described as linear combinations of doubly substituted (DS) configurations which overall yield four electrons in four singly occupied orbitals. Computed DS character of S(1), strongly correlated with facile (1)O(2) production, was presumed to occur via S(1)→T(1) intersystem crossing (ISC) of the sensitizer. Further confirmation of this relation was provided by newly synthesized BODIPY derivatives and comparison of spectroscopic properties of their dimers and monomers. Near-IR absorption, desired for potential photodynamic therapy applications, was not pursuable for bis-chromophores by the standard strategy of π-extension, as DS singlet states are destabilized. Decreased exchange coupling in π-extended cases appears to be responsible for this destabilization. Comparisons with iodine incorporated bis-BODIPYs suggest that the dynamics of (1)O(2) generation via DS S(1) states are qualitatively different from that via ISC originating from heavy atom spin-orbit coupling. Although red-shifting the absorption wavelength to enter the therapeutic window does not seem attainable for orthogonal bis-BODIPYs with DS S(1) states, modifications in the chromophore cores are shown to be promising in fine-tuning the excitation characteristics.
Citations by journals
|
1
2
3
4
5
6
7
8
|
|
|
Journal of Organic Chemistry
|
Journal of Organic Chemistry
8 publications, 7.08%
|
|
Organic Letters
|
Organic Letters
6 publications, 5.31%
|
|
Journal of Physical Chemistry C
|
Journal of Physical Chemistry C
6 publications, 5.31%
|
|
Dyes and Pigments
|
Dyes and Pigments
5 publications, 4.42%
|
|
Chemistry - A European Journal
|
Chemistry - A European Journal
5 publications, 4.42%
|
|
Journal of Physical Chemistry Letters
|
Journal of Physical Chemistry Letters
4 publications, 3.54%
|
|
Journal of Materials Chemistry C
|
Journal of Materials Chemistry C
4 publications, 3.54%
|
|
Chemical Communications
|
Chemical Communications
4 publications, 3.54%
|
|
Journal of Luminescence
|
Journal of Luminescence
3 publications, 2.65%
|
|
Journal of Physical Chemistry B
|
Journal of Physical Chemistry B
3 publications, 2.65%
|
|
Chemical Society Reviews
|
Chemical Society Reviews
3 publications, 2.65%
|
|
Physical Chemistry Chemical Physics
|
Physical Chemistry Chemical Physics
3 publications, 2.65%
|
|
Dalton Transactions
|
Dalton Transactions
3 publications, 2.65%
|
|
Organic and Biomolecular Chemistry
|
Organic and Biomolecular Chemistry
3 publications, 2.65%
|
|
Russian Journal of General Chemistry
|
Russian Journal of General Chemistry
2 publications, 1.77%
|
|
Journal of Chemical Physics
|
Journal of Chemical Physics
2 publications, 1.77%
|
|
Photochemical and Photobiological Sciences
|
Photochemical and Photobiological Sciences
2 publications, 1.77%
|
|
Scientific Reports
|
Scientific Reports
2 publications, 1.77%
|
|
Coordination Chemistry Reviews
|
Coordination Chemistry Reviews
2 publications, 1.77%
|
|
Angewandte Chemie - International Edition
|
Angewandte Chemie - International Edition
2 publications, 1.77%
|
|
Angewandte Chemie
|
Angewandte Chemie
2 publications, 1.77%
|
|
Chemistry - An Asian Journal
|
Chemistry - An Asian Journal
2 publications, 1.77%
|
|
ChemPhotoChem
|
ChemPhotoChem
2 publications, 1.77%
|
|
Journal of Physical Chemistry A
|
Journal of Physical Chemistry A
2 publications, 1.77%
|
|
Journal of Chemical Theory and Computation
|
Journal of Chemical Theory and Computation
2 publications, 1.77%
|
|
RSC Advances
|
RSC Advances
2 publications, 1.77%
|
|
Wiley Interdisciplinary Reviews: Computational Molecular Science
|
Wiley Interdisciplinary Reviews: Computational Molecular Science
1 publication, 0.88%
|
|
Journal of Porphyrins and Phthalocyanines
|
Journal of Porphyrins and Phthalocyanines
1 publication, 0.88%
|
|
International Journal of Molecular Sciences
|
International Journal of Molecular Sciences
1 publication, 0.88%
|
|
Frontiers in Chemistry
|
Frontiers in Chemistry
1 publication, 0.88%
|
|
1
2
3
4
5
6
7
8
|
Citations by publishers
|
5
10
15
20
25
30
35
40
|
|
|
American Chemical Society (ACS)
|
American Chemical Society (ACS)
36 publications, 31.86%
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
26 publications, 23.01%
|
|
Wiley
|
Wiley
21 publications, 18.58%
|
|
Elsevier
|
Elsevier
15 publications, 13.27%
|
|
Springer Nature
|
Springer Nature
7 publications, 6.19%
|
|
Pleiades Publishing
|
Pleiades Publishing
2 publications, 1.77%
|
|
American Institute of Physics (AIP)
|
American Institute of Physics (AIP)
2 publications, 1.77%
|
|
World Scientific
|
World Scientific
1 publication, 0.88%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 0.88%
|
|
Frontiers Media S.A.
|
Frontiers Media S.A.
1 publication, 0.88%
|
|
Societa Italiana di Fisica
|
Societa Italiana di Fisica, 1, 0.88%
Societa Italiana di Fisica
1 publication, 0.88%
|
|
5
10
15
20
25
30
35
40
|
- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2012,2013,2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["","","","","","","","","","","","",""],"datasets":[{"label":"Citations number","data":[3,9,8,9,8,11,13,11,14,14,4,5,4],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["2.65","7.96","7.08","7.96","7.08","9.73","11.5","9.73","12.39","12.39","3.54","4.42","3.54"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Journal of Organic Chemistry","Organic Letters","Journal of Physical Chemistry C","Dyes and Pigments","Chemistry - A European Journal","Journal of Physical Chemistry Letters","Journal of Materials Chemistry C","Chemical Communications","Journal of Luminescence","Journal of Physical Chemistry B","Chemical Society Reviews","Physical Chemistry Chemical Physics","Dalton Transactions","Organic and Biomolecular Chemistry","Russian Journal of General Chemistry","Journal of Chemical Physics","Photochemical and Photobiological Sciences","Scientific Reports","Coordination Chemistry Reviews","Angewandte Chemie - International Edition","Angewandte Chemie","Chemistry - An Asian Journal","ChemPhotoChem","Journal of Physical Chemistry A","Journal of Chemical Theory and Computation","RSC Advances","Wiley Interdisciplinary Reviews: Computational Molecular Science","Journal of Porphyrins and Phthalocyanines","International Journal of Molecular Sciences","Frontiers in Chemistry"],"ids":[8697,3315,8859,10101,24708,21963,3848,9073,7075,14990,20586,1773,8473,541,13581,544,2532,13767,13437,19215,25450,10120,25567,15255,58,3100,22866,9848,14627,6407],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/ARM4e6URKRsbRZvIF0vFis9DjxGloBjnBYJXbHmZ_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/jZQkhOOcY9wrGwZm7XGRwMe8H7fThQu3KamISuun_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp"],"datasets":[{"label":"","data":[8,6,6,5,5,4,4,4,3,3,3,3,3,3,2,2,2,2,2,2,2,2,2,2,2,2,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[7.08,5.31,5.31,4.42,4.42,3.54,3.54,3.54,2.65,2.65,2.65,2.65,2.65,2.65,1.77,1.77,1.77,1.77,1.77,1.77,1.77,1.77,1.77,1.77,1.77,1.77,0.88,0.88,0.88,0.88],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["American Chemical Society (ACS)","Royal Society of Chemistry (RSC)","Wiley","Elsevier","Springer Nature","Pleiades Publishing","American Institute of Physics (AIP)","World Scientific","Multidisciplinary Digital Publishing Institute (MDPI)","Frontiers Media S.A.","Societa Italiana di Fisica"],"ids":[40,123,11,17,8,101,250,23,202,208,802],"codes":[0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/ARM4e6URKRsbRZvIF0vFis9DjxGloBjnBYJXbHmZ_medium.webp","\/storage\/images\/resized\/jZQkhOOcY9wrGwZm7XGRwMe8H7fThQu3KamISuun_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp",""],"datasets":[{"label":"","data":[36,26,21,15,7,2,2,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[31.86,23.01,18.58,13.27,6.19,1.77,1.77,0.88,0.88,0.88,0.88],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Duman S. et al. Heavy Atom Free Singlet Oxygen Generation: Doubly Substituted Configurations Dominate S1 States of Bis-BODIPYs // Journal of Organic Chemistry. 2012. Vol. 77. No. 10. pp. 4516-4527.
GOST all authors (up to 50)
Copy
Duman S., Cakmak Y., Kolemen S., Akkaya E. U., Dede Y. Heavy Atom Free Singlet Oxygen Generation: Doubly Substituted Configurations Dominate S1 States of Bis-BODIPYs // Journal of Organic Chemistry. 2012. Vol. 77. No. 10. pp. 4516-4527.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo300051v
UR - https://doi.org/10.1021%2Fjo300051v
TI - Heavy Atom Free Singlet Oxygen Generation: Doubly Substituted Configurations Dominate S1 States of Bis-BODIPYs
T2 - Journal of Organic Chemistry
AU - Duman, Selin
AU - Cakmak, Yusuf
AU - Kolemen, Safacan
AU - Akkaya, Engin U.
AU - Dede, Yavuz
PY - 2012
DA - 2012/05/02 00:00:00
PB - American Chemical Society (ACS)
SP - 4516-4527
IS - 10
VL - 77
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex
Copy
@article{2012_Duman,
author = {Selin Duman and Yusuf Cakmak and Safacan Kolemen and Engin U. Akkaya and Yavuz Dede},
title = {Heavy Atom Free Singlet Oxygen Generation: Doubly Substituted Configurations Dominate S1 States of Bis-BODIPYs},
journal = {Journal of Organic Chemistry},
year = {2012},
volume = {77},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021%2Fjo300051v},
number = {10},
pages = {4516--4527},
doi = {10.1021/jo300051v}
}
Cite this
MLA
Copy
Duman, Selin, et al. “Heavy Atom Free Singlet Oxygen Generation: Doubly Substituted Configurations Dominate S1 States of Bis-BODIPYs.” Journal of Organic Chemistry, vol. 77, no. 10, May. 2012, pp. 4516-4527. https://doi.org/10.1021%2Fjo300051v.