Steering on-surface polymerization with metal-directed template

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1 Supporting Information Steering on-surface polymerization with metal-directed template Tao Lin 1, Xue Song Shang 2, Jinne Adisoejoso 1, Pei Nian Liu 2,*, Nian Lin 1,* 1. Synthesis Compounds 1 and 2 were prepared according to the method reported in the literature: Fleischer, E. B.; Shachter, A. M. Inorg. Chem. 1991, 30, Compound 4 (5,15-di(4-bromophenyl)-10,20-diphenylporphyrin) 5-(4-Nitrophenyl)dipyrromethane (5). Pyrrole( g, mmol) and 4- nitrobenzaldehyde (1 g, 6.62 mmol) were added to a 50 ml of two-necked round-bottomed flask and degassed with a stream of Ar for 5 min. Trifluoroacetic acid (75.48 mg, mmol) was then added, and the solution was stirred under Ar at room temperature for 5 min and then quenched with 0.1 M NaOH. Ethyl acetate was then added. The organic phasic was washed with water and dried over Na 2 SO 4, and the solvent was removed after filtration under reduced pressure. Pyrrole was recovered by reduced pressure distillation and the residue was passed through column chromatography (eluent: petroleum ether:ch 2 Cl 2 = 1:3) on silica gel to afford product 5 as green solid (1.022 g, 58% yield). Mp: o C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.17 (d, J = 8.76 Hz, 2H), 7.99 (br s, 2H), 7.37 (d, J = 8.60 Hz, 2H), (m, 2H), 6.18 (q, J = 3.08 Hz, 2H), 5.87 (s, 2H), 5.58 (s, 1H). S1

2 5,15-Di(4-nitrophenyl)-10,20-diphenylporphyrin (6). Compound 5 (0.5 g, 1.87 mmol), benzaldehyde (0.212 g, 2 mmol) and propanoic acid (35 ml) were refluxed in a 100 ml of round-bottomed flask for 2.5 h. The reaction mixture was then cooled and propanoic acid was removed by reduced pressure distillation. The residue was dissolved with chloroform and saturated K 2 CO 3 aqueous solution was added into the solution with slight stirring. Then the mixture was transferred to separating funnel and the organic phase was dried over Na 2 SO 4. After filtration, the solvent was evaporated under reduced pressure, and the residue was first passed through flash column chromatography on silica gel (eluent: CH 2 Cl 2 /CH 3 OH = 100:1) on silica gel and the obtained crude product was then passed through column chromatography on silica gel (eluent: CH 2 Cl 2 ) on silica gel to afford product 6 as purple crystals (133 mg, 20% yield). Mp >320 o C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.91 (d, J = 4.76 Hz, 4H), 8.76 (d, J = 4.76 Hz, 4H), 8.65 (d, J = 8.60 Hz, 4H), 8.40 (d, J = 8.56 Hz, 4H), 8.21 (d, J = 6.32 Hz, 4H), 7, (m, 6H), (s, 2H). 5,15-di(4-aminophenyl)-10,20-diphenylporphyrin (7). Compound 6 (133 mg, mmol) was dissolved in 30 ml of concentrated hydrochloric acid under argon. Tin(II) chloride dihydrate(260 mg, mmol) was added to the solution, and the mixture was heated to 65 o C for 1.5 h with stirring. The reaction mixture was cooled and cold water was added. Then the mixture was adjusted to ph 8-9 with concentrated ammonium hydroxide. The aqueous phase was extracted with chloroform and the obtained organic phase was dried over Na 2 SO 4. After filtration, the solvent was evaporated under reduced pressure, and the residue was passed through flash column chromatography on silica gel (eluent: CH 2 Cl 2 :CH 3 OH = 100:1) to give product 7 (39.3 mg, 32.27%). Mp >320 o C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.92 (d, J = 4.68 Hz, 4H), 8.82 (d, J = 4.68 Hz, 4H), (m, 4H), 7.99 (d, J = 8.28 Hz, 4H), (m, 6H), 7.06 (d, J = 8.32 Hz, 4H), 4.10 (s, 4H), (s, 2H). 5,15-di(4-bromophenyl)-10,20-diphenylporphyrin (4). Compound 7 (61.3 mg, mmol) was dissolved in 24 ml 50% H 2 SO 4 aq. and the mixture was stirring in cryohydrate bath. Sodium nitrite solution consisted of NaNO 2 (262 mg, 3.80 mmol) and H 2 O (12 ml) was slowly added into the porphyrin solution. The reaction was stirring for 10 min below 0 o C. Then urea (2.633 g, mmol) was added and the mixture was stirring for additional 10 min. After that, CuBr (272 mg, mmol) in cold hydrobromic acid (12 ml, 40.0%) was poured into the above reaction mixture and the reaction mixture was stirred for additional 2 h with the ice melting. Then the reaction mixture was diluted with water and the solution was adjusted to ph 10 with 3 M NaOH. The aqueous phase was extracted with chloroform and the obtained organic phase was dried over Na 2 SO 4. Column chromatography on silica gel (eluent: petroleum ether:ch 2 Cl 2 = 3:1) gives the crude product, which was recrystallized from chloroform/acetone to afford the product 4 as purple crystals (31.5 mg, 43% yield). Mp >320 o C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.86 (d, J = 4.72 Hz, 4H), 8.82 (d, J = 4.72 Hz, 4H), (m, 4H), 8.08 (d, J = 8.28 Hz, 4H), 7.89 (d, J = 8.28 Hz, 4H), (m, 6H), (s, 2H) ; HRMS (ESI, TOF) calcd for C 44 H 28 Br 2 N 4 [M + H] , found Kinetic Monte Carlo simulation The rates for hopping and rotation event are given by e p and S2

3 e p respectively, where is the attempt frequency, is the Boltzmann constant, and are the energy barriers of hopping and rotation for the free molecules. We adopt,, and in the simulation process S1. When one molecule attaches to another molecule in py-py configuration, a coordination bond is formed immediately. And when one molecule encounters another in Br-Br configuration, the rate of bond formation is given by e p. We adopt. When one molecule is bonded with other molecules, the hopping and rotation rates are given by e p and e p respectively, where and are the numbers of covalent and coordination bonds, and are the covalent and coordination bond energies. We adopt for the irreversible covalent bond and for the reversible coordination bond 33. Reference: S1 Buchner, F. et al. Diffusion, rotation, and surface chemical bond of individual 2Htetraphenylporphyrin molecules on Cu(111). J. Phys. Chem. C 115, (2011). 3. Self-assembly of 2 with Cu Molecule 2 uniquely forms 1D supramolecular single-row (SR) chains stabilized by py-cupy coordination. Fig. S1a shows a high-resolution STM topograph (up panel) and a structural model (low panel) of the SR chain. A common feature shared by these chains is that almost all of the resolved structures have one end attached to the atomic steps of the substrate, as shown in Fig. S1b. Hence steps on the substrate serve as nucleation sites for self-assembly and result in stable growth perpendicular to steps. The free ends often show a rather dynamic nature as subsequent STM-scans of the same chain often show different configurations, while the ends attached at the atomic steps remain immobilized. Frequently the chains are curved, implying a high-degree flexibility of the two-fold pyridyl-cu-pyridyl coordination. This bonding flexibility even allows a large section of chains to move on the surface without fragmenting the supramolecular structure. Fig. S1c shows such a dynamic example: two chains are anchored at a step edge while their free ends exhibit multiple features that arise from the shifting of the chain section during STM imaging. Examining the bond angles between adjacent monomers within a chain concludes that nearly 60% of the bonds have a 180 angle, while deviations from this ideal angle are well present, as shown in Fig. S1d. Note that there is a slight preference for a 120 angle, presumably due to the underlying Au(111) surface orientations. S3

4 Figure S1 Self-assembly of 2. (a) High resolution STM topograph (15 nm 15 nm) and structural model of sing-row (SR) chains stabilized by py-cu-py coordination. (b) STM topograph showing bent or curved chains. (c) STM topograph showing the free end of chains oscillating during scanning (scale bar 10 nm in b and c). (d) Statistical distribution of the angles between adjacent monomers in a chain. 4. Control experiments of adding 3. We deposited molecule 3 onto two samples: sample I was with SR chains formed out of molecule 1 at room temperature and sample II was with DR chains formed out of molecule 1 with 180 C annealing. We found that in both cases, two-dimensional network islands (marked by green rectangle) appear. Besides the 2D islands, sample I has SR chains only (Fig. S2a) and sample II DR chains only (Fig. S2b). So, the pre-existing SR or DR chains were not broadened into wider chains when molecules of 3 were added to the samples. Instead, the newly-formed 2D islands may link to the end of the pre-existing chains. Hence, these control experiments unambiguously indicate that in the SR or DR chains, the pyridyl functions are at the chain direction but not perpendicular to the chain direction. S4

5 Figure S2 Control experiment of adding 3. STM topographs (100 nm 100 nm) showing (a) adding 3 to a sample which was pre-covered by SR chains and (b) adding 3 to a sample which was pre-covered by DR chains. 5. Intermediate organometallic state. With a moderate annealing at 120 C, 1 and Cu form an intermediate state. In Fig. S3a, one can see a 3 3 square (missing a corner) in which the spacing between neighboring molecules in both directions is about 2 nm (cf. Fig. S3b). So, the molecules are not covalently bonded (Note the covalent coupling occurs above 150 C). In one direction, the molecules are linked via py-cupy coordination; whereas in the orthogonal direction, the molecules are linked by organomatellic bond, as illustrated in Fig. S3c. The presence of the protrusions at the side of the chain as marked by the arrow in Fig. S3a indicates the bromine atoms are at the side. And this is another evidence of the proposed structure. Figure S3 Intermediate structures formed out of 1 and Cu with 120 C annealing. (a) STM topograph (30 nm 30 nm) showing the intermediate structures. (b) Line profiles along two directions. (c) Structural model of the organometallic state. 6. Reactivity of 1 in the absence of Cu. To test the role of Cu in the coupling reaction, we prepared a sample deposited with 1 but without Cu. Fig S4a shows that at room temperature molecules of 1 self-assemble into large S5

6 monolayer patches on the Au(111) terraces. Fig S4b is a high-resolution STM image showing the molecules are arranged in a close-packed structure. This arrangement is almost identical to the structure formed out of 2 in the absence of Cu on Au(111) surface. A tentative structural model is overlaid in Fig. S4b. In this arrangement, the molecules interact with the neighboring ones via weak inter-molecular forces. After the sample was annealed at 180 C for 10 minutes, as shown in Fig. S4c, the close-packed islands are still present dominantly on the surface (>98% of total molecular coverage) and in addition, some small irregular islands appeared on the open terraces. However, no chain-like structures were identified. Within those irregular islands, the intermolecular spacing between some neighboring molecules was resolved by STM as 1.8 nm (cf. inset in Fig S3d), which is in the range of C-C coupled macromolecular porphyrin species. Since these irregular islands appeared after 180 C annealing, we conclude that these small irregular islands contain the covalently-bonded 1. By counting the coverage of the large-area closepacking islands and the small irregular islands, we can estimate that the upper limit of C-C bond formation ration is 1.5%. Figure S4 (a) STM topograph (200 nm 200 nm) showing the large area molecular monolayer formed by 1 on Au(111) in the absence of Cu. (b) High-resolution STM showing the closepacked structure with a tentative molecular model. (c) STM topograph (200 nm 200 nm) showing the sample of (a) with an annealing treatment at 180 C for 10 minutes. An irregular island is circled. (d) High-resolution STM of an irregular island and line profile showing shorter inter-molecular distance (inset). S6

7 7. Macromolecular structures formed out of 4. Fig S5 shows a sample of molecule 4 and Cu annealed at 180 C for different duration. The STM topographs were acquired at 200 K. After 3 minutes annealing, the molecules formed macromolecular chains (Fig. S7a), which consist of molecules linked by covalent bonds. By extending the annealing duration to 30 minutes, the size and density of the macromolecular chains increased apparently (Fig. S7b). Figure S5 STM topographs (100 nm 100 nm) showing the macromolecular structures formed out of 4 and Cu on Au(111) with 3 minutes (a) and 30 minutes annealing (3). Data acquired at 200 K. 8. Effects of annealing (duration and temperature). Fig S6 a-c show the STM topographs of a sample with molecule 1 and Cu with different annealing duration at 180 C. After 3 minutes annealing, more than half of the molecules is still involved in SR chains (Fig. S6a), i.e. they are un-reacted species. By extending the annealing duration to 30 minutes, most of the molecules are in DR or TR chains (Fig. S6b). Further extending the annealing time (60 minutes) does not change the structures remarkably (Fig. S6c). Fig. S6d shows the weight distributions of the three cases. One can see the clear contrast between the 3-min annealed sample and the 30-min annealed sample, while the 30-min and 60-min annealed ones exhibit very similar characteristics. S7

8 Figure S6 Structures formed out of 1 with annealing treatment at 180 C for different duration. (a)-(c) Sample annealed for 3, 30 and 60 minutes, respectively. (100 nm 100 nm) (d) Weight distribution of the macromolecular structures of (a)-(c). We annealed samples of 1 with Cu to different temperatures sequentially as shown in Fig. S7. With 150 C annealing, most of the molecules are un-reacted and SR chains are present predominantly. The coupling reaction takes place at 180 C and DR chains are the most popular macromolecular structures. Further increasing the annealing temperature does not widen the chains significantly. In other words, the DR chains are always the most popular macromolecular structures with higher temperature annealing treatments. S8

9 Fig S7 Structures formed out of 1 with sequential annealing treatment at different temperature. (a)-(f) Sample annealed at 150 C, 180 C, 210 C, 240 C, 270 C and 300 C, respectively. Each annealing step lasted for three minutes. (100 nm 100 nm) 9. Simulated polymerization process of 1. Movie S1 shows time sequence frames of the simulated polymerization process of compound 1. It displays that most of the C-C bonds are formed between the neighboring monomers that were anchored to the existing chains though coordination bonds. It also displays that once a monomer is covalently-attached to the side of a chain, a new row is developed from it quickly. S9

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