TY - JOUR
T1 - Synthesis of Structurally Diverse Emissive Molecular Rotors with Four-Component Ugi Stators
AU - García-González, Ma Carmen
AU - Aguilar-Granda, Andrés
AU - Zamudio-Medina, Angel
AU - Miranda, Luis D.
AU - Rodríguez-Molina, Braulio
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/3/2
Y1 - 2018/3/2
N2 - The use of the multicomponent Ugi reaction to rapidly prepare a library of dumbbell-like molecular rotors is highlighted here. The synthetic strategy consisted of the atom-economic access to 15 bulky and structurally diverse iodinated stators, which were cross-coupled to the 1,4-diethynylphenylene rotator. From those experiments, up to six rotors 1a-c and 1l-n were obtained, with yields ranging from 35 to 69% per coupled C-C bond. In addition to the framework diversity, five of these compounds showed aggregate-enhanced emission properties thanks to their conjugated 1,4-bis(phenylethynyl)benzene cores, a property that rises by increasing the water fraction (fw) in their THF solutions. The results highlight the significance of the diversity-oriented synthesis of rapid access to new molecular fluorescent rotors.
AB - The use of the multicomponent Ugi reaction to rapidly prepare a library of dumbbell-like molecular rotors is highlighted here. The synthetic strategy consisted of the atom-economic access to 15 bulky and structurally diverse iodinated stators, which were cross-coupled to the 1,4-diethynylphenylene rotator. From those experiments, up to six rotors 1a-c and 1l-n were obtained, with yields ranging from 35 to 69% per coupled C-C bond. In addition to the framework diversity, five of these compounds showed aggregate-enhanced emission properties thanks to their conjugated 1,4-bis(phenylethynyl)benzene cores, a property that rises by increasing the water fraction (fw) in their THF solutions. The results highlight the significance of the diversity-oriented synthesis of rapid access to new molecular fluorescent rotors.
UR - http://www.scopus.com/inward/record.url?scp=85042847593&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b02858
DO - 10.1021/acs.joc.7b02858
M3 - Artículo
C2 - 29457731
SN - 0022-3263
VL - 83
SP - 2570
EP - 2581
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -