J. Wu, A. Fechtenkötter, J. Gauss, M. D. Watson, M. Kastler et al., Controlled Self-Assembly of Hexa-Peri-Hexabenzocoronenes in Solution, J. Am. Chem. Soc, vol.126, pp.11311-11321, 2004.

J. Wu, M. Baumgarten, M. G. Debije, J. M. Warman, and K. Müllen, Arylamine-Substituted Hexa-Peri-Hexabenzocoronenes: Facile Synthesis and Their Potential Applications as, Coaxial" Hole-Transport Materials. Angew. Chemie -Int, vol.43, pp.5331-5335, 2004.

J. Wu, M. D. Watson, and K. Müllen, The Versatile Synthesis and Self-Assembly of Star-Type Hexabenzocoronenes. Angew. Chemie Int, vol.42, pp.5329-5333, 2003.

M. Lee, J. Kim, S. Peleshanko, K. Larson, Y. Yoo et al.,

, Amphiphilic Hairy Disks with Branched Hydrophilic Tails and a Hexa-Peri-Hexabenzocoronene Core, J. Am. Chem. Soc, vol.124, pp.9121-9128, 2002.

J. Wu, J. Li, U. Kolb, and K. Müllen, A Water-Soluble Hexa-Peri-Hexabenzocoronene: Synthesis, Self-Assembly and Role as Template for Porous Silica with Aligned Nanochannels, Chem. Commun, vol.0, pp.48-50, 2006.

L. Schmidt-mende, A. Fechtenkötter, K. Müllen, E. Moons, R. H. Friend et al., Self-Organized Discotic Liquid Crystals for High-Efficiency Organic Photovoltaics, Science, vol.293, pp.1119-1122, 2001.

A. J. Fleming, J. N. Coleman, A. B. Dalton, A. Fechtenko, M. D. Watson et al., Optical Spectroscopy of Isolated and Aggregate Hexabenzocoronene Derivatives: A Study of Self-Assembling Molecular Nanowires, J. Phys. Chem. B, vol.107, pp.37-43, 2003.

W. Pisula, ?. Tomovi?, B. El-hamaoui, M. D. Watson, T. Pakula et al., Control of the Homeotropic Order of Discotic Hexa-Peri-Hexabenzocoronenes, Adv. Funct. Mater, vol.15, pp.893-904, 2005.

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I. O. Shklyarevskiy, P. Jonkheijm, N. Stutzmann, D. Wasserberg, H. J. Wondergem et al., High Anisotropy of the Field-Effect Transistor Mobility in Magnetically Aligned Discotic Liquid-Crystalline Semiconductors, J. Am. Chem. Soc, vol.127, pp.16233-16237, 2005.

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T. Ml-of and . Meoh, /1) in a two-necked round-bottom flask. The solution was cooled down to 0°C and 2.67 ml of ICl (1 M in DCM) were added and left 1 hour under stirring at room temperature. After quenching with Na2S2O3 (1 M, around 10 ml), the organic phase was separated and washed 3 times with water before evaporation of the solvents. The product is purified with column chromatography with cyclohexane and after evaporation of the solvent, vol.867

H. Nmr, , vol.2

. Maldi-tof-ms-m/z, Iodo-5'-(trimethylsilyl)-1,1':4',1''-terphenyl 34 (0.1 g, 0.23 mmol) was introduced in a dry round-bottom flask, degassed by two vaccum-argon cycles and left two hours under vaccum. 15 ml of dry THF were introduced and cooled down to -78°C. The n-BuLi solution (0.175 ml, 0.35 mmol, 1 M in cyclohexane) was added dropwise and the solution turned yellow, Synthesis of acid -5'-(trimethylsilyl)-1,1':4',1''-terphenyl-2'-boronic ester, vol.36

, H NMR (? in ppm, 400MHz, CDCl3): 7.61 (s, 1H, a), 7.57 (s, 1H, b)

. Maldi-tof-ms-m/z, Synthesis of 3,3'-di(trimethylsilyl)-2,5,2',5'-tetraphenylbiphenyl 35: Boronic ester 36 (200 mg, 0.47 mmol), iodo-terphenyl 34 (300 mg, 0.7 mmol), Palladium acetate (55 mg, 0.24 mmol), SPhos (190 mg, 0.47 mmol) and Potassium phosphate tribasic (198 mg, 0.93 mmol) were introduced in a dry round-bottom flask and degassed by three vaccum-argon cycles. 6 ml of Toluene and 1 ml of water were added and degassed by 3 "freeze-pump-thaw" and the reaction was left at 60°C overnight. The dark solution obtained was extracted with DCM

H. Nmr,

. Maldi-tof-ms-m/z, Experimental part 3,3'-di(trimethylsilyl)-2,5,2',5'-tetraphenylbiphenyl 35 (150 mg, 0.25 mmol) was introduced in a dry 25 ml round-bottom flask and dezaged with two vaccum-argon cycles. Then 5 ml of DCM were added and the solution was cooled down to 0°C, vol.37

, The reaction was quenched with a saturated solution of sodium thiosulfate, the product was extracted with DCM and washed twice with water. The organic phase was evaporated and the solide was purified by column chromatography with a mixture of cyclohexane and DCM (70/30). The pure product was obtained as 108 mg of a yellowish powder, mmol) was added and the reaction was left overnight at room temperature under argon

H. Nmr, , vol.400

. Maldi-tof-ms-m/z, Synthesis of 3,3'-bis(ethynyltrimethylsilane)-2,5,2

, 07 mmol) were introduced in a dry three neck roundbottom flask and degassed with two vacuum-argon cycles. Then 10 ml of toluene and 15 ml of Et3N were introduced and the solution was degassed with two "freeze-pump-thaw". The ethynyltrimathylsilane (48 µL, 0.34 mmol) was then introduced dropwise and the solution was Chapter 6: Experimental part left at 80°C overnight. The solution was filtered on celite and the product was extracted with DCM, washed with water twice and dried with sodium sulfate, and Pd(PPh3)2Cl2 (49 mg

H. Nmr, 400MHz, CDCl3): 7.55-7.53 (m, 4H, a), 7.46 (s, 2H, b)

. Maldi-tof-ms-m/z, 3'-bis(ethynyltrimethylsilane)-2,5,2',5'-tetraphenylbiphenyl 38 (50 mg, 0.077 mmol) was introduced in a Schlenck flask and degassed with to vacuum-argon cycles and THF (3 ml) was introduced. The Bu4NF was then added (184 µL, 0.18 mmol) and the solution was left 2h at ambient temperature. The product was extracted with DCM and washed with water twice dendrimer, Experimental part MALDI-TOF MS m/z: calcd, vol.32

H. Nmr,

. Maldi-tof-ms-m/z,

, Dendrimer 39 (56 mg, 0.030 mmol) was dispersed in non-stabilized DCM and the solution was degassed with argon for 30min, Separetly, FeCl3 (691 mg, p.4

. Maldi-tof-ms-m/z, The main peak found is the 3,3',5,5'-tetra(ethynyltrimethylsilane)-1,1'

. Pd, Experimental part 3,3',5,5'-tetraethynyl-1,1'-biphenyl 40 (30 mg; 0,12 mmol) and tetraphenylcyclopentadienone (253 mg; 0,66 mmol) were added to diphenylether (1 ml) in a dry Schlenk flask and heated at 180 °C overnight. The viscous product was diluted with 1 ml of dichloromethane and added dropwise to cold ethanol (200 ml). The product was filtered and dried under vacuum. The powder was first purified with column chromatography with toluene to get rid of Ph2O. The second purification was done on column chromatography with a mixture of cyclohexane and DCM (7/1), vol.6

H. Nmr,

. Maldi-tof-ms-m/z, Synthesis of GNRod 13 8 : Dendrimer 42 (50 mg, 0.22 mmol) was dispersed in 120 ml of non-stabilized DCM in a twonecked round-bottom flask of 250 ml, p.27

. Maldi-tof-ms-m/z, Experimental part Synthesis of GNRod 19 4 : GNRod 13 (20 mg, 0.012 mmol) and AlCl3 (6.6 mg, 0.049 mmol) were introduced in a dry two necked round-bottom flask (100 ml), and dissolved on 20 ml of CCl4. After 20 min of argon bubbling, ICl (0.37 ml, 7.4 mmol) was added and the reaction was left for 48h at 80°C. The reaction was quenched with ethanol and then, calcd for C132H34: 1618, vol.27

. Maldi-tof-ms-m/z, Experimental part 3,3',5,5'-tetraethynyl-1,1'-biphenyl 41 (30 mg; 0,12 mmol) and 3,4-bis(4-dodecylphenyl)-2,5-diphenylcyclopentadienone (253 mg; 0,66 mmol) were added to o-xylene (2 ml) in a dry Schlenk flask and heated at 180 °C overnight. The viscous product was diluted with 1 ml of dichloromethane and added dropwise to cold ethanol (200 ml). The precipitate was filtered and dried under vacuum. The purification was done with column chromatography with a mixture of, Synthesis of dendrimer 43, vol.87

, H NMR (? in ppm, 400MHz, CDCl3): 7.16-6.33 (m, 82H)

. Maldi-tof-ms-m/z, Synthesis of GNRod, vol.20

, Dendrimer 43 (50 mg, 0.22 mmol) was dispersed in 120 ml of non-stabilized DCM in a twonecked round-bottom flask of 250 ml, Separetly, p.27

. Maldi-tof-ms-m/z, Copper iodide (80.4 mg, 0.42 mmol), triphenylphosphin (116 mg, 0.44 mmol) and Pd(PPh3)2Cl2 (148.7 mg, 0.21 mmol) were introduced in a three necked round-bottom flask and degassed by two vaccum-argon cycles. Synthesis of 2',5'-bis(trimethylsilyl)-3',3''biphenyl-1,1':4',1''-terphenyl 48: DiiododiTMSbenzene 25 (1 g, 2.1 mmol), 2-biphenylboronic acid (1.25 g, 6.33 mmol), Potassium carbonate (1.34 g, 6.33 mmol), SPhos (170 mg, 0.42 mmol) and Pd(OAc)2 (47 mg, 0.21 mmol) were introduced in a dry three necked round-bottom flask. The powders were degassed by 3 vaccum-argon cycles. 30 ml of toluene and 5 ml of water were mixed and degassed by 3 "freeze-pump-thaw". After addition of the solvents, the reaction was left at 80°C overnight. The dark solution obtained was extracted with DCM, Tribromobenzene (500 mg, 1.6 mmol), vol.46

H. Nmr, , vol.2

. Maldi-tof-ms-m/z, biphenyl-1,1':4',1''-terphenyl 49: 2',5'-bis(trimethylsilyl)-3',3''biphenyl-1,1':4',1''-terphenyl 48 (0.1 g, 0.19 mmol) was introduced in a dry round-bottom flask and degassed by two vaccum-argon cycles. Then 5 ml of DCM were added and the solution was cooled down to 0°C and degassed with argon bubbling for 10min. The ICl solution (0.76 ml, 1M in DCM, 0.76 mmol) was then added dropwise and the reaction was left under stirring at ambient temperature under argon Chapter 6: Experimental part overnight. The reaction was quenched with a sodium sulfate solution (1 M, about 10 ml) and the product was extracted with DCM and washed twice with water

H. Nmr,

. Maldi-tof-ms-m/z, Synthesis of 2',5'-bis(3,5-bis(ethynyltrimetylsilane)-phenyl)-3',3''biphenyl-1,1':4',1''-terphenyl 50: 2',5'-diiodo-3, vol.3, p.5

, 84 mmol) were introduced in a schlenk flash and degassed with two vaccum-argon cycles. Toluene (18 ml), ethanol (6 ml) and water (3 ml) were added and degassed with three Freeze-pump-thaw. The reaction was left 24 hours at 80°C under argon. The solution was filtered on celite with DCM and washed twice with water, SPhos (215 mg, 0.52 mmol) and potassium carbonate (1.08 g, 7

H. Nmr,

. Maldi-tof-ms-m/z, biphenyl-1,1':4',1''-terphenyl 44: Compound 50 (150 mg, 0.16 mmol) was introduced in a dry schlenk flask and degassed with two vaccum-argon cycles. 20 ml of THF and TBAF (0.82 ml, 0.82 mmol, 1 M in THF) were added and the reaction was left 1 hour at 0°C. The product was extracted with DCM and washed twice with water and the organic phase was evaporated. The product was precipitated in methanol and filtered to obtain 95 mg of powder (94% yield). dendrimer 45: Precursor 44 (150 mg, 0.24 mmol) and tetraphenylcyclopentadienone (400 mg, 1.1 mmol) were introduced in a dry schlenk flask and degassed by two vaccum-argon cycles. The o-xylene (5 ml) was added and the reaction was left at 180°C overnight. The solution was then

, H NMR (? in ppm, 400MHz, CDCl3): 7.42-7.28 (m, 10H), 7.22-6.64 (m, 100H)

. Maldi-tof-ms-m/z, After addition of the FeCl3 solution, the mixture was left 20 hours under argon coming from a two necked round-bottom flask filled with DCM in which argon was bubbling. The solution was quenched with methanol (about 40 ml) and then filtered on PTFE and washed with methanol, vol.14

. Maldi-tof-ms-m/z, After 20 min of argon bubbling, ICl (2.1 g, 13 mmol) were added and the reaction was left for 72h at 85°C. The reaction was quenched with ethanol and ICl and CCl4 were evaporated at about 60°C with a liquid nitrogen trap. The solid obtained after evaporation of the solvents was solubilized with DCM and precipitated in methanol. The precipitate was then washed with methanol and purified by column chromatography in chloroform

. Maldi-tof-ms-m/z, Experimental part Precursor 50 (15 mg, 0.024 mmol) and tetraphenylcyclopentadienone (82 mg, 0.11 mmol) were introduced in a dry schlenk flask and degassed by two vaccum-argon cycles. The o-xylene (5 ml) was added and the reaction was left at 180°C overnight. The solution was then added dropwise to cold ethanol (about 200 ml) and the precipitate was filtered. This solide was purified with multiple recrystalisations in methanol, vol.51

, H NMR (? in ppm, 400MHz, CDCl3): 7.40-7.28 (m, 12H), 7.21-6.51 (m, 90, p.16

. Maldi-tof-ms-m/z,

, After addition of the FeCl3 solution, the mixture was left 20 hours under argon coming from a two necked round-bottom flask filled with DCM in which argon was bubbling. The solution was quenched with methanol (about 40 ml) and then filtered on PTFE and washed with methanol

. Maldi-tof-ms-m/z, Anhydrous dimethylformamide (DMF) (200mL) and copper (20g, 312.5mmol) were introduced and the solution was stirred at 160°C overnight. After cooling down to 120°C the solution was filtered on celite. The product was washed 3 times with DMF and the filtrate was then poured in a, vol.9, p.3

, 5%) under stirring. The black solid was filtered and washed with the diluted ammonium Chapter

H. Nmr,

. Maldi-tof-ms-m/z, calcd for C18H9N3O6: 363.05, vol.5, pp.9-52

H. Nmr,

, Triiodotriphenylene 54 12 : 1,5,9-Trinitrotriphenylene 53 (0.2g, 0.73mmol) was introduced in a 25 ml round-bottom flask with 2 ml of HCl (3M) and 2 ml of water. The solution was cooled down to 0°C and a solution of sodium nitrite (1.45 M, 2 ml) was added dropwise under stirring. The resulting solution was added to a solution of sodium iodide, MALDI-TOF MS m/z calcd for C18H9NH2: 273.13, found: 274.13 (M+H) + . Synthesis of 1, vol.5

H. Nmr, , vol.400, pp.9-21

. Maldi-tof-ms-m/z, Synthesis of 1,3,5-tris(2'-trimethylsilyl-1,1':4',1''-terphenyl)benzene 55: Iodoterphenyltrimethylsilane 34 (1.24 g, 2.89 mmol), Acid phenyltriboronic ester (400 mg, 0.87 mmol), Palladium acetate (6.5 mg, 0.029 mmol), SPhos (23.8 mg, 58 mmol) and Potassium phosphate tribasic (1.23 g, 5.7 mmol) were introduced in a 25 ml Schlenk flask and degassed with three vaccum-argon cycles. The solution was left overnight at 100°C under argon and filtered on celite with DCM before evaporation of the solvents. The product was purified with recrystallisation in cyclohexane and

H. Nmr,

. Maldi-tof-ms-m/z, Experimental part 1,3,5-tris(2'-trimethylsilylterphenyl)benzene 55 (350 mg, 0.35 mmol) was introduced in 30 ml of DCM in a two-necked round-bottom flask. The solution was degassed with argon bubbling for 15min and cooled down to 0°C. The ICl (2.1 ml, 2.1 mmol, 1 M in nitromethane) was added dropwise and the solution was left overnight under stirring at room temperature. The reaction was quenched with Na2S2O3 (1 M, 20 ml) and the product was extracted with DCM, washed twice with water and brine. After evaporation of the solvent, the product is purified with column chromatography with a mixture of cyclohexane and ethyl acetate (2%), vol.56

, H NMR (? in ppm, 400MHz, CDCl3): 7.97-7.89 (m, 3H), 7.46-7.32 (m, 15H), 7.17-6.49 (m, 21H)

. Maldi-tof-ms-m/z,

F. Silly, A Robust Method for Processing Scanning Probe Microscopy Images and Determining Nanoobject Position and Dimensions, J. Microsc, vol.236, pp.211-218, 2009.

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V. S. Iyer, M. Wehmeier, J. Diedrich, M. A. Keegstra, and K. Müllen, From Hexa-Peri-Hexabenzocoronene to "Superacenes, Angew. Chemie -Int, vol.36, pp.1603-1607, 1997.

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?. Tomovi?, M. D. Watson, and K. Müllen, Superphenalene-Based Columnar Liquid Crystals. Angew. Chemie -Int, vol.43, pp.755-758, 2004.

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F. E. Golling, M. Quernheim, M. Wagner, T. Nishiuchi, and K. Müllen, Concise Synthesis of 3D ?-Extended Polyphenylene Cylinders. Angew. Chemie -Int, vol.53, pp.1525-1528, 2014.

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W. Pisula, E. Tomovi, C. Simpson, M. Kastler, T. Pakula et al., Relationship between Core Size, Side Chain Length, and the Supramolecular Organization of Polycyclic Aromatic Hydrocarbons, Chem. Mater, vol.17, pp.4296-4303, 2005.

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