Segmented graphene nanoribbons

A segmented graphene nanoribbon, comprising:

• at least two different graphene segments covalently linked to each other;
• wherein each graphene segment has a monodisperse segment width;
• wherein the segment width of at least one of the graphene segments is 4 nm or less,
• wherein the two or more different graphene segments have repeating units which are derived from substituted or unsubstituted anthracene monomer compounds and
• wherein the segmented graphene nanoribbon has the structure Ia:
• under the provision that at least two of m, x, n, y, o, z, and p are ≥1;
• and
• m+x+n+y+o+z+p≥10;
• and wherein
• X are each independently H, a halogen, SH, SR3, OH, OR3, OSO2R3, (SO)R3, (SO2)R3, NR1R2, NO2, POR3R3, PO(OR3)R3, PO(OR3)2, B(R3)2, B(OR3)2, (CO)R3, (CO)OR3;
• Y are each independently H or two Y together form a direct bond between neighbouring repeating units;
• R are each independently hydrogen;
• linear or branched or cyclic C1-C12alkyl which is unsubstituted or substituted by one or more OH, C1-C4alkoxy, phenyl, or by CN;
• C2-C12alkyl which is interrupted by one or more non-consecutive O;
• halogen;
• OH;
• OR3;
• SR3;
• CN;
• NO2;
• NR1R2;
• (CO)R3;
• (CO)OR3;
• O(CO)OR3;
• O(CO)NR1R2;
• O(CO)R3;
• C1-C12alkoxy:
• C1-C12alkylthio;
• (C1-C6alkyl)-NR7R8;
• or —O—(C1-C6alkyl)NR1R2;
• aryl or heteroaryl (wherein aryl is preferably phenyl, biphenyl, naphthyl, or anthryl all of which are unsubstituted or are substituted by one or more C1-C4-alkyl, CN, OR3, SR3, CH2OR3, (CO)OR3, (CO)NR1R2 or halogen);
• or two R together with the carbon atoms they are attached to form a 5-8-membered cycle or heterocycle;
• R1 and R2 are each independently hydrogen, linear or branched C1-C6alkyl or phenyl, or R1 and R2 together with the nitrogen atom to which they are bonded to form a group selected from
• and
• R3 is H, C1-C12alkyl, phenyl which is unsubstituted or is substituted by one or more C1-C4alkyl, phenyl, halogen, C1-C4alkoxy or C1-C4alkylthio.

A segmented graphene nanoribbon, comprising:

• at least two different graphene segments covalently linked to each other;
• wherein each graphene segment has a monodisperse segment width;
• wherein the segment width of at least one of the graphene segments is 4 nm or less,
• wherein two or more different graphene segments have repeating units which are derived from substituted or unsubstituted pentacene monomer compounds and
• wherein the segmented graphene nanoribbon has the structure II:
• under the provision that at least two of m, x, n, y, o, z, and p are ≥1;
• wherein m+x+n+y+o+z+p≥10;
• and wherein
• X are each independently H, a halogen, SH, SR3, OH, OR3, OSO2R3, (SO)R3, (SO2)R3, NR1R2, NO2, POR3R3, PO(OR3)R3, PO(OR3)2, B(R3)2, B(OR3)2, (CO)R3, (CO)OR3;
• Y are each independently H or two Y together form a direct bond between neighbouring repeating units;
• R are each independently hydrogen;
• linear or branched or cyclic C1-C12alkyl which is unsubstituted or substituted by one or more OH, C1-C4alkoxy, phenyl, or by CN;
• C2-C12alkyl which is interrupted by one or more non-consecutive O;
• halogen;
• OH;
• OR3;
• SR3;
• CN;
• NO2;
• NR1R2;
• (CO)R3;
• (CO)OR3;
• O(CO)OR3;
• O(CO)NR1R2;
• O(CO)R3;
• C1-C12alkoxy:
• C1-C12alkylthio;
• (C1-C6alkyl)-NR7R8;
• or —O—(C1-C6alkyl)NR1R2;
• aryl or heteroaryl (wherein aryl is preferably phenyl, biphenyl, naphthyl, or anthryl all of which are unsubstituted or are substituted by one or more C1-C4-alkyl, CN, OR3, SR3, CH2OR3, (CO)OR3, (CO)NR1R2 or halogen);
• or two R together with the carbon atoms they are attached to form a 5-8-membered cycle or heterocycle;
• R1 and R2 are each independently hydrogen, linear or branched C1-C6alkyl or phenyl, or R1 and R2 together with the nitrogen atom to which they are bonded to form a group selected from
• and
• R3 is H, C1-C12alkyl, phenyl which is unsubstituted or is substituted by one or more C1-C4alkyl, phenyl, halogen, C1-C4alkoxy or C1-C4alkylthio.

A segmented graphene nanoribbon, comprising:

• at least two different graphene segments covalently linked to each other;
• wherein each graphene segment has a monodisperse segment width;
• wherein the segment width of at least one of the graphene segments is 4 nm or less,
• wherein two or more different graphene segments have repeating units which are derived from substituted or unsubstituted anthracene and pentacene monomer compounds and
• wherein the segmented graphene nanoribbon has the structure IV:
• wherein m+n≥0,
• and wherein
• X are each independently H, a halogen, SH, SR3, OH, OR3, OSO2R3, (SO)R3, (SO2)R3, NR1R2, NO2, POR3R3, PO(OR3)R3, PO(OR3)2, B(R3)2, B(OR3)2, (CO)R3, (CO)OR3;
• R are each independently hydrogen;
• linear or branched or cyclic C1-C12alkyl which is unsubstituted or substituted by one or more OH, C1-C4alkoxy, phenyl, or by CN;
• C2-C12alkyl which is interrupted by one or more non-consecutive O;
• halogen;
• OH;
• OR3;
• SR3;
• CN;
• NO2;
• NR1R2;
• (CO)R3;
• (CO)OR3;
• O(CO)OR3;
• O(CO)NR1R2;
• O(CO)R3;
• C1-C12alkoxy:
• C1-C12alkylthio;
• (C1-C6alkyl)-NR7R8;
• or —O—(C1-C6alkyl)NR1R2;
• aryl or heteroaryl (wherein aryl is preferably phenyl, biphenyl, naphthyl, or anthryl all of which are unsubstituted or are substituted by one or more C1-C4-alkyl, CN, OR3, SR3, CH2OR3, (CO)OR3, (CO)NR1R2 or halogen);
• or two R together with the carbon atoms they are attached to form a 5-8-membered cycle or heterocycle;
• R1 and R2 are each independently hydrogen, linear or branched C1-C6alkyl or phenyl, or R1 and R2 together with the nitrogen atom to which they are bonded to form a group selected from
• wherein R1 is a different structure than R2;
• and
• R3 is H, C1-C12alkyl, phenyl which is unsubstituted or is substituted by one or more C1-C4alkyl, phenyl, halogen, C1-C4alkoxy or C1-C4alkylthio.

A segmented graphene nanoribbon, comprising:

• at least two different graphene segments covalently linked to each other;
• wherein each graphene segment has a monodisperse segment width;
• wherein the segment width of at least one of the graphene segments is 4 nm or less,
• wherein two or more different graphene segments have repeating units derived from substituted and/or unsubstituted naphthalene monomer compounds and
• wherein the segmented graphene nanoribbon has the structure V:
• under the provision that at least two of m, x, and n are ≥1;
• wherein m+x+n are ≥10;
• and wherein
• X are each independently H, a halogen, SH, SR3, OH, OR3, OSO2R3, (SO)R3, (SO2)R3, NR1R2, NO2, POR3R3, PO(OR3)R3, PO(OR3)2, B(R3)2, B(OR3)2, (CO)R3, (CO)OR3;
• Y are each independently H or two Y together form a direct bond between neighbouring repeating units;
• R are each independently hydrogen;
• linear or branched or cyclic C1-C12alkyl which is unsubstituted or substituted by one or more OH, C1-C4alkoxy, phenyl, or by CN;
• C2-C12alkyl which is interrupted by one or more non-consecutive O;
• halogen;
• OH;
• OR3;
• SR3;
• CN;
• NO2;
• NR1R2;
• (CO)R3;
• (CO)OR3;
• O(CO)OR3;
• O(CO)NR1R2;
• O(CO)R3;
• C1-C12alkoxy:
• C1-C12alkylthio;
• (C1-C6alkyl)-NR7R8;
• or —O—(C1-C6alkyl)NR1R2;
• aryl or heteroaryl (wherein aryl is preferably phenyl, biphenyl, naphthyl, or anthryl all of which are unsubstituted or are substituted by one or more C1-C4-alkyl, CN, OR3, SR3, CH2OR3, (CO)OR3, (CO)NR1R2 or halogen);
• or two R together with the carbon atoms they are attached to form a 5-8-membered cycle or heterocycle;
• R1 and R2 are each independently hydrogen, linear or branched C1-C6alkyl or phenyl, or R1 and R2 together with the nitrogen atom to which they are bonded to form a group selected from
• and
• R3 is H, C1-C12alkyl, phenyl which is unsubstituted or is substituted by one or more C1-C4alkyl, phenyl, halogen, C1-C4alkoxy or C1-C4alkylthio.

A segmented graphene nanoribbon, comprising:

• at least two different graphene segments covalently linked to each other;
• wherein each graphene segment has a monodisperse segment width;
• wherein the segment width of at least one of the graphene segments is 4 nm or less,
• wherein at least one of the segments has a substituted or unsubstituted repeating unit with N1=5 and at least one of the segments has a substituted or unsubstituted repeating unit with N2=10 or 15, wherein Ni and N2 are the number of dimer lines across the segment width and
• wherein the segmented graphene nanoribbon has the structure XI:
• under the proviso that at least one m, p, q, r, s, u, v, w, and x is ≥1, and at least one of n, o, and t is ≥1;
• wherein m+n+o+p+q+r+s+t+u+v+w+x≥10;
• and wherein
• X are each independently H, a halogen, SH, SR3, OH, OR3, OSO2R3, (SO)R3, (SO2)R3, NR1R2, NO2, POR3R3, PO(OR3)R3, PO(OR3)2, B(R3)2, B(OR3)2, (CO)R3, (CO)OR3;
• Y are each independently H or two Y together form a direct bond between neighbouring repeating units.

A segmented graphene nanoribbon, comprising:

• at least two different graphene segments covalently linked to each other;
• wherein each graphene segment has a monodisperse segment width;
• wherein the segment width of at least one of the graphene segments is 4 nm or less,
• wherein at least one of the segments has a substituted or unsubstituted repeating unit with N1=7 and at least one of the segments has a substituted or unsubstituted repeating unit with N2=14 or 21, wherein N1 and N2 are the number of dimer lines across the segment width and
• wherein the segmented graphene nanoribbon has the structure If:
• under the proviso that at least one of m, p, q, w, x, r, s, u, and v are ≥1, and at least one of n, o, and t are ≥1;
• wherein m+n+o+p+q+r+s+t+u+v+w+x≥10;
• and wherein
• X are each independently H, a halogen, SH, SR3, OH, OR3, OSO2R3, (SO)R3, (SO2)R3, NR1R2, NO2, POR3R3, PO(OR3)R3, PO(OR3)2, B(R3)2, B(OR3)2, (CO)R3, (CO)OR3;
• Y are each independently H or two Y together form a direct bond between neighbouring repeating units.