TY - JOUR
T1 - Synthesis and Spectral Properties of 8-Anilinonaphthalene-1-sulfonic Acid (ANS) Derivatives Prepared by Microwave-Assisted Copper(0)-Catalyzed Ullmann Reaction
AU - Wang, Nan
AU - Faber, Erik B.
AU - Georg, Gunda I.
PY - 2019/11/5
Y1 - 2019/11/5
N2 - 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.
AB - 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.
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U2 - 10.1021/acsomega.9b03002
DO - 10.1021/acsomega.9b03002
M3 - Article
C2 - 31720551
AN - SCOPUS:85074263842
VL - 4
SP - 18472
EP - 18477
JO - ACS Omega
JF - ACS Omega
SN - 2470-1343
IS - 19
ER -