Polycyclic aromatic bridges for molecular electronic sensors
AssigneeSemiconBio Inc.
InventorsBarry Merriman, Tim Geiser, Paul W. Mola, Darryl Rideout
Life of this patent
Estimating the term…
Abstract
In various embodiments, synthetic bridge molecules are disclosed, usable in molecular electronics sensors. In various aspects, bridge molecules comprise fused ring polycyclic aromatic hydrocarbon structures in the shape of a long and narrow ribbon, with end groups on opposite short ends for selective binding to metal electrodes, one or more substituents near the midpoint of a long edge for binding to a probe molecule, and one or more additional substituent groups for solubility or other effects. In various embodiments, the bridge molecules herein are conducting, and provide a closed circuit in a sensor when forming a bridge between gapped electrodes.
Claims10
A synthetic bridge molecule for use in a molecular electronics sensor, the molecule comprising the structure:
- wherein:
- n and m are independently 0 to 30;
- W and Y are independently selected from —O—, —CH2-, CR8R9, CH2CR8R9, CR8CR9CH2, OCR8R9 and CR8R9O, wherein R8 and R9 are attached to the same carbon atom and independently selected from H, CH3, C2H5, CH2CH2CH3, or (CH2)X(OCH2CH2)YOR10, wherein x is 2 to 10, y is 10 to 40 and R10 is H, Me, or Et, and wherein R8 and R9 can optionally link to form a ring, wherein O is optionally linked directly to the aromatic ring, and wherein W and Y can optionally be exchanged with one another within a ring;
- W′ and Y′ are independently selected from —O—, —CH2-, CR8R9CH2CR8R9, CR8CR9CH2, OCR8R9, and CR8R9O, wherein R8 and R9 are attached to the same carbon atom and independently selected from H, CH3, C2H5, CH2CH2CH3, or (CH2)X(OCH2CH2)YOR10, wherein x is 2 to 10, y is 10 to 40 and R10 is H, Me, or Et, and wherein R8 and R9 can optionally link to form a ring, wherein O is optionally linked directly to the aromatic ring, and wherein W′ and Y′ can optionally be exchanged with one another within a ring;
- R1 is a moiety selected from (i) ester linked PEG chains (CH2)xCO(OCH2CH2)yOR13 or CH2)xOC═OCH2CH2CH2(OCH2CH2)yOR13, wherein x is from 0 to 10, y is from 10 to 40, and R13 is Me or H;
- or (ii) a water-soluble, ester-linked dendron comprising 8 to 64 branches, each derivatized with water-solubilizing PEG chains of structure (CH2CH2O)zR14 wherein z is from 1 to 8 and R14 is H or Me, wherein the ester-linkage of R1 optionally comprises a 1) photocleavable, 2) redox-cleavable, 3) acid cleavable or 4) base-cleavable linker such that the dendron can be removed using 1) light, 2) an oxidizing or reducing agent, 3) an acid or 4) a base, respectively;
- R2 s a moiety selected from (i) ester linked PEG chains (CH2)xCO(OCH2CH2)yOR13 or (CH2)xOC═OCH2CH2CH2(OCH2CH2)yOR13 wherein x is from 0 to 10, y is from 10 to 40, and R13 is Me or H, ii) a water-soluble, ester-linked dendron linked from the nanoribbon with 4 to 16 branches, each devitalized with water-solubilizing PEG chains (CH2CH2O)zR14 wherein z is from 1 to 4 and R14 is H or Me, wherein the ester-linkage of R2 optionally comprises a 1) photocleavable, 2) redox-cleavable, 3) acid cleavable or 4) base-cleavable linker such that the dendron can be removed using 1) light, 2) an oxidizing or reducing agent, 3) an acid or 4) a base, respectively;
- W″ and Y″ are independently selected from —S—, —CH2—, CH2CH2, CR11R12, and SCR11R12, wherein R11 and R12 are bonded to the same carbon atom and independently selected from H, CH3, C2H5, CH2CH2CH3, CH2CH2SCH3, SCH3, or SCH2CH2SCH3, and wherein R8 and R9 can optionally link to form a ring, wherein S is optionally linked directly to the aromatic ring, and wherein W″ and Y″ can optionally be exchanged with one another within a ring;
- R5 is H, SMe, or CH2CH2SMe;
- R6 is H, SMe, SCH2CH2SMe, SCH2C(CH2SMe)3, SH, CS2H, CH2SMe, CH2SH, CH2CS2H, 6[1,3-diisopropyl-1H-benzo[d]imidazol-3-ium]-yl or 6-[1,3-diisopropyl-1H-benzo[d]imidazol-3-ium]-thioyl;
- and
- R7 is H, SMe, SCH2CH2SMe, SH, CS2H, CH2SMe, CH2SH, CH2CS2H, 6-[1,3-diisopropyl-1H-benzo[d]imidazol-3-ium]-yl or 6-[1,3-diisopropyl-1H-benzo[d]imidazol-3-ium]-thioyl.
Dependencies are inferred from the claim text.