Synthesis and Spectral Properties of 8‑Anilinonaphthalene-1-sulfonic
Acid (ANS) Derivatives Prepared by Microwave-Assisted Copper(0)-Catalyzed
Ullmann Reaction
Version 2 2019-11-18, 19:08Version 2 2019-11-18, 19:08
Version 1 2019-10-28, 12:05Version 1 2019-10-28, 12:05
Posted on 2019-11-18 - 19:08
For
decades, the dye 8-anilino-1-naphthalenesulfonic acid (ANS)
has been used to study biological systems due to its environmentally
sensitive fluorescent nature and propensity to bind to hydrophobic
pockets of proteins. However, the syntheses of ANS and its derivatives
have been low yielding, requiring harsh reaction conditions and long
reaction times. We have developed efficient, mild microwave-assisted
copper(0)-catalyzed Ullmann coupling conditions to synthesize ANS
derivatives with yields of up to 74%. Many of these derivatives have
spectral properties distinct from ANS, including improved and diminished
quantum yields, different absorption and emission maxima, and complete
loss of fluorescence. ANS derivatives with these unique fluorescence
properties are useful tools to study biological systems.
CITE THIS COLLECTION
DataCite
DataCiteDataCite
3 Biotech3 Biotech
3D Printing in Medicine3D Printing in Medicine
3D Research3D Research
3D-Printed Materials and Systems3D-Printed Materials and Systems
4OR4OR
AAPG BulletinAAPG Bulletin
AAPS OpenAAPS Open
AAPS PharmSciTechAAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität HamburgAbhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)ABI Technik (German)
Academic MedicineAcademic Medicine
Academic PediatricsAcademic Pediatrics
Academic PsychiatryAcademic Psychiatry
Academic QuestionsAcademic Questions
Academy of Management DiscoveriesAcademy of Management Discoveries
Academy of Management JournalAcademy of Management Journal
Academy of Management Learning and EducationAcademy of Management Learning and Education
Academy of Management PerspectivesAcademy of Management Perspectives
Academy of Management ProceedingsAcademy of Management Proceedings
Academy of Management ReviewAcademy of Management Review
Wang, Nan; Faber, Erik B.; Georg, Gunda I. (2019). Synthesis and Spectral Properties of 8‑Anilinonaphthalene-1-sulfonic
Acid (ANS) Derivatives Prepared by Microwave-Assisted Copper(0)-Catalyzed
Ullmann Reaction. ACS Publications. Collection. https://doi.org/10.1021/acsomega.9b03002