التفاصيل البيبلوغرافية
| العنوان: |
Bis-Rhodamines Bridged with a Diazoketone Linker: Synthesis, Structure, and Photolysis |
| المؤلفون: |
Heydar Shojaei (2485579), Mariano L. Bossi (1808740), Vladimir N. Belov (476840), Stefan W. Hell (101918) |
| سنة النشر: |
2021 |
| المجموعة: |
Smithsonian Institution: Digital Repository |
| مصطلحات موضوعية: |
Biophysics, Biochemistry, Physiology, Pharmacology, Plant Biology, Chemical Sciences not elsewhere classified, Physical Sciences not elsewhere classified, short photoreactive bridge, pendant phenyl rings, moderate fluorescence increase, gave mainly α, insufficient quenching ability, bulky dye residues, position 5 ′, 5 , wolff rearrangement ), 6 , 2 , 2 , 1 , wolff rearrangement, 6 ′, 5 ′-, parent dye, migration ability, rhodamines bridged, remained unexplored, ph 7, fascinating structures, diazoketone linker |
| الوصف: |
Two fluorophores bound with a short photoreactive bridge are fascinating structures and remained unexplored. To investigate the synthesis and photolysis of such dyes, we linked two rhodamine dyes via a diazoketone bridge (−COCN 2 −) attached to position 5′ or 6′ of the pendant phenyl rings. For that, the mixture of 5′- or 6′-bromo derivatives of the parent dye was prepared, transformed into 1,2-diarylacetylenes, hydrated to 1,2-diarylethanones, and converted to diazoketones Ar 1 COCN 2 Ar 2 . The high performance liquid chromatography (HPLC) separation gave four individual regioisomers of Ar 1 COCN 2 Ar 2 . Photolysis of the model compoundC 6 H 5 COCN 2 C 6 H 5 in aqueous acetonitrile at pH 7.3 and under irradiation with 365 nm light provided diphenylacetic acid amide (Wolff rearrangement). However, under the same conditions, Ar 1 COCN 2 Ar 2 gave mainly α-diketones Ar 1 COCOAr 2 . The migration ability of the very bulky dye residues was low, and the Wolff rearrangement did not occur. We observed only moderate fluorescence increase, which may be explained by the insufficient quenching ability of diazoketone bridge (−COCN 2 −) and its transformation into another (weaker) quencher, 1,2-diarylethane-1,2-dione. |
| نوع الوثيقة: |
article in journal/newspaper |
| اللغة: |
unknown |
| Relation: |
https://figshare.com/articles/journal_contribution/Bis-Rhodamines_Bridged_with_a_Diazoketone_Linker_Synthesis_Structure_and_Photolysis/17268679 |
| DOI: |
10.1021/acs.joc.1c01721.s001 |
| الاتاحة: |
https://doi.org/10.1021/acs.joc.1c01721.s001 |
| Rights: |
CC BY-NC 4.0 |
| رقم الانضمام: |
edsbas.5C9B925D |
| قاعدة البيانات: |
BASE |