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1. (WO2011159763) ALKYNYL-SUBSTITUTED INDENOFLUORENES USEFUL IN ELECTRONIC AND ELECTRO-OPTICAL DEVICES
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What is claimed is:

1. A compound having a structure of:


or


(Formula 2)

wherein R1 - R12 are each individually h, amino, alkynyl, substituted alkynyl, halogen, alkyl, aryl, substituted alkyl, substituted aryl, nitro, alkoxy, substituted heteroaryl, cycloalkyl, or substituted cycloalkyl, provided that at least two of R 1 - R 12 are alkynyl or substituted alkynyl.

2. The compound of claim 1, wherein the compound is of formula 1 and R -R4 and R7-R10 are each individually H, amino, halogen, alkyl, aryl, substituted alkyl, substituted aryl, nitro, alkoxy, substituted alkoxy, cyano, thiol, substituted thiol, thioether, hydroxyl, heteroaryl, substituted heteroaryl, cycloalkyl, or substituted cycloalkyl; and

R5, R6, R11 and R12 are each individually H, alkynyl, substituted alkynyl, amino, halogen, alkyl, aryl, substituted alkyl, substituted aryl, nitro, alkoxy, substituted alkoxy, cyano, thiol, thioether, hydroxyl, heteroaryl, substituted heteroaryl, cycloalkyl, or substituted cycloalkyl, provided that at least two of R5, R6,

R 11 and R 12 are alkynyl or substituted alkynyl.

3. The compound of claim 1, wherein the compound is of formula 2, and Rx-R4 and R7-R10 are each individually H, amino, halogen, alkyl, aryl, substituted alkyl, substituted aryl, nitro, alkoxy, substituted alkoxy, cyano, thiol, substituted thiol, thioether, hydroxyl, heteroaryl, substituted heteroaryl, cycloalkyl, or substituted cycloalkyl; and

R5 and Rn are each individually alkynyl or substituted alkynyl.

4. The compound of claim 2, wherein R6 and R12 are each alkynyl or substituted alkynyl.

5. The compound of claim 2, wherein R5, R6, R11 and R12 are each alkynyl or substituted alkynyl.

6. The compound of any one of claims 1 to 5, wherein the alkynyl is ethynyl or the substituted alkynyl is substituted ethynyl.

7. The compound of any one of claims 1 to 5, wherein the substituted alkynyl is substituted with a silyl, an alkyl silyl, an aryl silyl, an alkoxy silyl, a tin-containing group, or a germanium-containing group.

8. The compound of any one of claims 1 to 7, wherein R1, R3, R4, R7,

R 9", and R 110U are each H, and R 2 and R 8 are each individually amino, halogen, alkyl, aryl, substituted alkyl, substituted aryl, nitro, alkoxy, substituted alkoxy, cyano, thiol, substituted thiol, thioether, hydroxyl, heteroaryl, substituted heteroaryl, cycloalkyl, or substituted cycloalkyl.

9. The compound of claim 8, wherein R 2 and R 8 are identical moieties.

10. The compound of any one of claims 1 to 7, wherein R1, R4, R7, and

R 10 are each H, and R 2", R 3J, R 8° and R 9" are each individually amino, halogen, alkyl, aryl, substituted alkyl, substituted aryl, nitro, alkoxy, substituted alkoxy, cyano, thiol, substituted thiol, thioether, hydroxyl, heteroaryl, substituted heteroaryl, cycloalkyl, or substituted cycloalkyl.

11. The compound of claim 10, wherein R 2 , R 3 , R 8 and R 9 are identical moieties.

12. The compound of any one of claims 1 to 7, wherein R1, R2, R4, R7,

R 8 , and R 10 are each H, and R 3 and R 9 are each individually amino, halogen, alkyl, aryl, substituted alkyl, substituted aryl, nitro, alkoxy, substituted alkoxy, cyano, thiol, substituted thiol, thioether, hydroxyl, heteroaryl, substituted heteroaryl, cycloalkyl, or substituted cycloalkyl.

13. The compound of claim 12, wherein R 3 and R 9 are identical moieties.

14 Th d f f l i 1 7 h i R 3 R 2 R 4 R 8

aryl, substituted alkyl, substituted aryl, nitro, alkoxy, substituted alkoxy, cyano, thiol, substituted thiol, thioether, hydroxyl, heteroaryl, substituted heteroaryl, cycloalkyl, or substituted cycloalkyl.

15. The compound of claim 14, wherein R 1 and R 7 are identical moieties.

16. The compound of any one of claims 1 to 7, wherein Rx-R4 and R7-Ru are each individually H.

17. The compound of any one of claims 1 to 7, wherein Rx-R4 and R7-Ru are each individually H, and two of R5, R6, R11 and R12 are each individually amino, halogen, alkyl, aryl, substituted alkyl, substituted aryl, nitro, alkoxy, substituted alkoxy, cyano, thiol, thioether, hydroxyl, heteroaryl, substituted heteroaryl, cycloalkyl, or substituted cycloalkyl.

18. The compound of claim 17, wherein R5 and R6 or R11 and R12 are identical moieties.

19. The compound of any one claims 1 to 7, wherein at least two of R1-R4 and R7-R10 are not H.

20. The compound of any one of claims 1 to 5, wherein each alkynyl or substituted alkynyl is the identical moiety.

21. An indenofluorene that includes at least two alkynyl-containing substituents.

22. The indenofluorene of claim 21, wherein the alkynyl-containing substituents are bonded directly to a carbon atom of the indenofluorene ring.

23. The indenofluorene of claim 21 or 22, wherein the indenofhiorene is indeno [ 1 ,2-b] fluorene .

24. The indenofluorene of claim 23, wherein the alkynyl-containing substituents are located at the 5, 6, 11 or 12 positions of indeno[1,2-b]fluorene.

25. The indenofluorene of claim 23, wherein the alkynyl-containing substituents are located at the 6 and 12 positions of indeno[1,2-b]fluorene; the 5 and 11 positions of indeno[1,2-b]fluorene; or 5, 6, 11 and 12 positions of indeno[1,2-b]fluorene.

26. The indenofluorene of claim 21 or 22, wherein the indenofluorene further includes two oxo substituents.

27. The indenofluorene of claim 26, wherein the oxo substituents are located at the 6 and 12 positions of the indenofluorene.

28. The indenofluorene of any one of claims 21 to 27, wherein the alkynyl-containing substituents also include a moiety selected from silyl, an alkyl silyl, an aryl silyl, an alkoxy silyl, a tin-containing group, or a germanium-containing group.

29. The indenofluorene of any one of claims 21 to 28, wherein the indenofluorene is substituted with an electron-withdrawing group or an electron-donating group at at least the 1, 2, 3, 4, 7, 8, 9, or 10 positions of indenofluorene.

30. The indenofluorene of claim 29, wherein the indenofluorene is substituted with an electron- withdrawing group or an electron-donating group at the 1 and 7 positions of indenofluorene, or the 2 and 8 positions of indenofluorene.

31. The indenofluorene of claim 21, wherein the alkynyl-containing substituents also include a silyl moiety or a substituted silyl moiety.

32. An electronic or electrooptical device that includes the compound of claim 1 or the indenofluorene of claim 21.

33. The device of claim 32, wherein the device is an organic light-emitting diode (OLED), an organic field-effect transistor (OFET), or an organic photovoltaic cell (OPV).

34. The device of claim 32, wherein the compound of claim 1 or the indenofluorene of claim 21 is an n-type organic semiconductor.

35. The device of claim 32, wherein the device is an organic photovoltaic cell (OPV).

36. The device of claim 32, wherein the device is an organic light-emitting diode (OLED), or an organic field-effect transistor (OFET).

37. A method for making an alkynyl-substituted indeno[1,2-b]fluorene, comprising:

reacting a dione- substituted indenofluorene with an alkyne to produce a hydroxy-functional intermediate; and

reducing the hydroxy-functional intermediate to produce an alkynyl-substituted indeno[ 1 ,2-b]fluorene.