Hydroxycruciforms: amine-responsive fluorophores.
The synthesis of three hydroxy-substituted cruciforms (XF, 1,4-bis(4'-hydroxystyryl)-2,5-bis(4''-methoxyphenylethynyl)benzene, 1,4-bis(4'-methoxystyryl)-2,5-bis(4''-hydroxyphenylethynyl)benzene, and 1,4-bis(4'-hydroxystyryl)-2,5-bis(4''-hydroxyphenylethynyl)benzene) starts with a Horner reaction followed by a Sonogashira coupling and subsequent deprotection. The three herein described XFs contain either two or four free phenolic hydroxyl groups. All three XFs were subjected to photometric UV/Vis titrations in a methanol/water mixture. The respective pK(a) values were obtained by data deconvolution. As the three XFs display a significant change in emission color upon photoinduced deprotonation, the XFs were taken up in different solvents and exposed to twelve amines. The amine-dependent change in emissivity of the tetrahydroxy XF is sufficiently distinct in the eight solvents that all of the inspected amines are discerned by a linear discriminant analysis. The tetrahydroxy XF in different solvents forms a sensor array, the response of which is based on the excited-state proton transfer (ESPT) to amines and mediated by the choice of the battery of solvents that are utilized.
McGrier
Psaras L
PL
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA.
Solntsev
Kyril M
KM
Miao
Shaobin
S
Tolbert
Laren M
LM
Miranda
Oscar R
OR
Rotello
Vincent M
VM
Bunz
Uwe H F
UH
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D000588:Amines; D001555:Benzene Derivatives; D005456:Fluorescent Dyes; D010636:Phenols; D013267:Stilbenes