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US 9,133,234 B2Granted
Functionalized naphthalene fluorophores
AssigneeKay M. Brummond
InventorsKay M. Brummond, Laura S. Kocsis, Erica Benedetti
Life of this patent
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Abstract
Methods for the synthesis and use of functionalized, substituted naphthalenes are described. The functionalized, substituted naphthalenes display useful properties including liquid crystals and fluorescence properties, such as solvatochromatic fluorescence, with high quantum yields, Stoke's shift, and show emission maxima that are significantly red-shifted.
Claims7
A functionalized naphthalene fluorophore having a structure:
- a) 1-(5-(dimethylamino)-2′,2′-dimethyl-1,3-dihydrospiro[cyclopenta[b]naphthalene-2,5′-[1,3] dioxan]-9-yl)ethanone;
- b) 1-(5-(dimethylamino)-2′,2′-dimethyl-1,3-dihydrospiro[cyclopenta[b]naphthalene-2,5′-[1,3] dioxan]-9-yl)-2,2-dimethylpropan-1-one;
- c) 1-(2,2-bis(((tert-butyldimethylsilyl)oxy)methyl)-8-(dimethylamino)-2,3-dihydro-1H-cyclo-penta[b]naphthalen-4-yl)ethanone;
- d) 1-(2′,2′-dimethyl-5-(pyrrolidin-1-yl)-1,3-dihydrospiro [cyclopenta[b]naphthalene-2,5′-[1,3]dioxan]-9-yl)ethanone;
- e) 1-(8-(dimethylamino)-2,2-bis(hydroxymethyl)-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)ethanone;
- f) 1-(8-(dimethylamino)-2,2-bis(hydroxymethyl)-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)-2,2-dimethylpropan-1-one;
- g) 1-(2,2-bis(hydroxymethyl)-8-(pyrrolidin-1-yl)-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)ethanone;
- h) (8-(dimethylamino)-4-pivaloyl-2,3-dihydro-1H-cyclopenta[b]naphthalene-2,2-diyl)bis (methylene)bis(undec-10-enoate);
- i) 6-((tert-butyldimethylsilyl)oxy)-1-(8-(dimethylamino)-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)hexan-1-one;
- j) 1-(8-(dimethylamino)-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)-6-hydroxyhexan-1-one;
- k) 9-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)-7-(dimethylamino)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- l) 7-(dimethylamino)-9-(4-(2-hydroxyethoxy)phenyl)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- m) 9-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-7-(dimethylamino)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- n) 7-(dimethylamino)-9-(4-(hydroxymethyl)phenyl)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- o) 2-(4-(6-dimethylamino)-3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)benzyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H) dione;
- p) 1-(4-(6-(dimethylamino)-3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)benzyl)-1H-pyrrole-2,5-dione;
- q) ethyl 2-((tert-butoxycarbonyl)amino)-3-41-(4-(6-(dimethylamino)-3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)benzyl)-2,5-dioxopyrrolidin-3-yl)thio)propanoate;
- r) 4-(6-(dimethylamino)-3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)benzaldehyde;
- s) 7-(dimethylamino)-9-(4-ethynylphenyl)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- t) methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(4-(6-(dimethylamino)-3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)phenyl)-1H-1,2,3-triazol-1-yl)propanoate;
- u) 4-(6-(dimethylamino)-3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-4-yl)benzylundec-10-enoate;
- v) 5-(Dimethylamino)-9-phenyl-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- w) 6-(Dimethylamino)-9-phenyl-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- x) 5-(Dimethylamino)-9-(trimethylsilyl)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- y) 6-(Dimethylamino)-9-(trimethylsilyl)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- z) 5-(Dimethylamino)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- aa) 6-(Dimethylamino)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one;
- or
- bb) 8-(Dimethylamino)-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one.
26 more elements
A functionalized naphthalene fluorophore having a structure:
- where R1 is a substituent selected from the group consisting of H, C1-C20 alkyl, C1-C20 alkoxy, an NMR active isotope or an alkyl or alkoxy group comprising an NMR active isotope, a substituted silyl, trialkylsilyl, diphenylalkylsilyl, triphenylalkylsilyl, a substituted phosphorous, dialkylphosphino, diphenylphosphino, phenyl, substituted phenyl, aryl, substituted aryl, heteroaryl, —S(O)R4, —S(O)2R4, P(O)(OR4)2, and —C(Y)R4 where Y is O, NR5, or S;
- each R2 is a halogen, an NMR active isotope or an alkyl or alkoxy group comprising an NMR active isotope, a substituted silyl, trialkylsilyl, diphenylalkylsilyl, triphenylalkylsilyl, a substituted phosphorous, dialkylphosphino, diphenylphosphino, or —N(R6)2;
- each R3 is H, C1-C20 alkyl, an NMR active isotope or an alkyl or alkoxy group comprising an NMR active isotope, a substituted silyl, trialkylsilyl, diphenylalkylsilyl, triphenylalkylsilyl, a substituted phosphorous, dialkylphosphino, diphenylphosphino, or combined as ═O;
- each R4, R5 and R6 is independently selected from H, C1-C20 alkyl, C1-C20 alkoxy, a substituted silyl, trialkylsilyl, diphenylalkylsilyl, triphenylalkylsilyl, a substituted phosphorous, dialkylphosphino, diphenylphosphino, an NMR active isotope or an alkyl or alkoxy group comprising an NMR active isotope, substituted or unsubstituted phenyl, aryl, heteroaryl, benzyl, or two R6 groups on an R2 group may come together to form a cyclic structure;
- X is CH2, C(R6)2, C(CO2Alkyl)2, O, NTs, NH, NCOR5 or NR5;
- n is an integer from 0 to 2;
- m is an integer from 1 to 4, provided that either R1 is one of —S(O)R4, —S(O)2R4, P(O)(OR4)2, and —C(Y)R4 or the R3 groups are combined as ═O wherein the NMR isotope is selected from 2H, 13C, 19F, or 31P.
4 more elements
Dependencies are inferred from the claim text.