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US 9,102,703 B2Granted
Synthesis, structure and use of functionalized naphthalenes
AssigneeKay M. Brummond
InventorsKay M. Brummond, Laura S. Kocsis, Erica Benedetti
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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.
Claims15
A functionalized naphthalene having a structure
- where R1 is a substituent selected from the group consisting of H, C1-C20 alkyl, C1-C20 alkoxy, phenyl, 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 or —N(R6)2;
- each R3 is H, C1-C20 alkyl, or combined as ═O;
- each R4, R5 and R6 is independently selected from H, C1-C20 alkyl, C1-C20 alkoxy, 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.
5 more elements
A fluorescent sensor comprising:
- a functionalized, substituted naphthalene having a structure:
- where R1 is a substituent selected from the group consisting of H, C1-C20 alkyl, C1-C20 alkoxy, phenyl, 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 or —N(R6)2;
- each R3 is H, C1-C20 alkyl, or combined as ═O;
- each R4, R5 and R6 is independently selected from H, C1-C20 alkyl, C1-C20 alkoxy, 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.
6 more elements
A solvatochromic fluorophore comprising:
- a functionalized, substituted naphthalene having a structure:
- where R1 is a substituent selected from the group consisting of H, C1-C20 alkyl, C1-C20 alkoxy, phenyl, 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 or —N(R6)2;
- each R3 is H, C1-C20 alkyl, or combined as ═O;
- each R4, R5 and R6 is independently selected from H, C1-C20 alkyl, C1-C20 alkoxy, 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.
6 more elements
Dependencies are inferred from the claim text.