Creation of Superheterojunction Polymers via Direct Polycondensation: Segregated and Bicontinuous Donor-Acceptor π-Columnar Arrays in Covalent Organic Frameworks for Long-Lived Charge Separation

Journal of the American Chemical Society

Volumn 137, Issue 24, 2015, Pages 7817-7827

  Jin, Shangbin ^a   Supur, Mustafa ^c   Addicoat, Matthew ^e   Furukawa, Ko ^d   Chen, Long ^a,b   Nakamura, Toshikazu ^a   Fukuzumi, Shunichi ^c   Irle, Stephan ^e   Jiang, Donglin ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b BEIJING INSTITUTE OF TECHNOLOGY   (China)

^c OSAKA UNIVERSITY   (Japan)

^d NIIGATA UNIVERSITY   (Japan)

^e NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; COPPER; ELECTRON TRANSITIONS; ELECTRONS; HETEROJUNCTIONS; MACHINERY; MAGNETIC MOMENTS; METALS; NAPHTHALENE; ORGANIC POLYMERS; POLYCONDENSATION; POLYMERIZATION; SEPARATION; SPIN DYNAMICS; X RAY DIFFRACTION; ZINC COMPOUNDS;

COVALENT ORGANIC FRAMEWORKS; DIRECT POLYCONDENSATION; ELECTRON DONOR ACCEPTORS; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOCHEMICAL DYNAMICS; STRUCTURAL SIMULATIONS; TIME-RESOLVED TRANSIENT ABSORPTION SPECTROSCOPY; X-RAY DIFFRACTION MEASUREMENTS;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

COPPER; COVALENT ORGANIC FRAMEWORK; METAL ORGANIC FRAMEWORK; METALLOPHTHALOCYANINE; NAPHTHALENE; NAPHTHALENE DIIMIDE; NICKEL; PERYLENE DIIMIDE; PHTHALOCYANINE; PHTHALOCYANINE ZINC; POLYMER; PYROMMELLITIC DIIMIDE; UNCLASSIFIED DRUG; IMIDE; INDOLE DERIVATIVE; METAL; NAPHTHALENE DERIVATIVE; NAPHTHALENEDIIMIDE; ORGANOMETALLIC COMPOUND; PERYLENE; PERYLENEDIIMIDE;

ABSORPTION SPECTROSCOPY; ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CONCEPTUAL FRAMEWORK; COVALENT BOND; CRYSTAL STRUCTURE; DIRECT POLYCONDENSATION; ELECTRIC CURRENT; ELECTRON; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; GEOMETRY; PHASE SEPARATION; PHOTOCHEMISTRY; POLYCONDENSATION; POLYMERIZATION; REACTION ANALYSIS; REACTION TIME; SEPARATION TECHNIQUE; STRUCTURE ANALYSIS; X RAY DIFFRACTION; ANALOGS AND DERIVATIVES; CHEMISTRY; MOLECULAR DYNAMICS;

ELECTRONS; IMIDES; INDOLES; METALS; MOLECULAR DYNAMICS SIMULATION; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; PERYLENE; POLYMERS; X-RAY DIFFRACTION;

EID: 84933056237     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b03553     Document Type: Article

References (50)

1. Feng, X.; Ding, X.; Jiang, D. Chem. Soc. Rev. 2012, 41, 6010-6022
2. Feng, X.; Chen, L.; Honsho, Y.; Saengsawang, O.; Liu, L.; Wang, L.; Saeki, A.; Irle, S.; Seki, S.; Dong, Y. P.; Jiang, D. Adv. Mater. 2012, 24, 3026-3031
3. Jin, S.; Ding, X.; Feng, X.; Supur, M.; Furukawa, K.; Takahashi, S.; Addicoat, M.; El-Khouly, E. M.; Nakamura, T.; Irle, S.; Fukuzumi, S.; Nagai, A.; Jiang, D. Angew. Chem., Int. Ed. 2013, 52, 2017-2021
4. Jin, S.; Furukawa, K.; Addicoat, M.; Chen, L.; Takahashi, S.; Irle, S.; Nakamura, T.; Jiang, D. Chem. Sci. 2013, 4, 4505-4511
5. Côté, A. P.; Benin, A.; Ockwig, N.; O'Keeffe, M.; Matzger, A.; Yaghi, O. M. Science 2005, 310, 1166-1170
6. Côté, A. P.; El-Kaderi, H. M.; Furukawa, H.; Hunt, J. R.; Yaghi, O. M. J. Am. Chem. Soc. 2007, 129, 12914-12915
7. Tilford, R. W.; Gemmill, W. R.; zur Loye, H. C.; Lavigne, J. J. Chem. Mater. 2006, 18, 5296-5301
8. Nagai, A.; Guo, Z.; Feng, X.; Jin, S.; Chen, X.; Ding, X.; Jiang, D. Nat. Commun. 2011, 2, 536 10.1038/ncomms1542
9. Wan, S.; Guo, J.; Kim, J.; Ihee, H.; Jiang, D. Angew. Chem., Int. Ed. 2008, 47, 8826-8830
10. Wan, S.; Guo, J.; Kim, J.; Ihee, H.; Jiang, D. Angew. Chem., Int. Ed. 2009, 48, 5439-5442
11. Ding, X.; Guo, J.; Feng, X.; Honsho, Y.; Guo, J. D.; Seki, S.; Maitarad, P.; Saeki, A.; Nagase, S.; Jiang, D. Angew. Chem., Int. Ed. 2011, 50, 1289-1293
12. Ding, X.; Chen, L.; Honso, Y.; Feng, X.; Saengsawang, O.; Guo, J. D.; Saeki, A.; Seki, S.; Irle, S.; Nagase, S.; Parasuk, V.; Jiang, D. J. Am. Chem. Soc. 2011, 133, 14510-14513
13. Feng, X.; Chen, L.; Dong, Y. P.; Jiang, D. Chem. Commun. 2011, 47, 1979-1981
14. Feng, X.; Liu, L.; Honsho, Y.; Saeki, A.; Seki, S.; Irle, S.; Dong, Y. P.; Nagai, A.; Jiang, D. Angew. Chem., Int. Ed. 2012, 51, 2618-2622
15. Ding, X.; Feng, X.; Saeki, A.; Seki, S.; Nagai, A.; Jiang, D. Chem. Commun. 2012, 48, 8952-8954
16. Feng, X.; Dong, Y. P.; Jiang, D. CrystEngComm. 2013, 15, 1508-1511
17. Chen, X.; Addicoat, M.; Irle, S.; Nagai, A.; Jiang, D. J. Am. Chem. Soc. 2013, 135, 546-549
18. Guo, J.; Xu, Y.; Jin, S.; Chen, L.; Kaji, T.; Honsho, Y.; Addicoat, M.; Kim, J.; Saeki, A.; Ihee, H.; Seki, S.; Irle, S.; Hiramoto, M.; Gao, J.; Jiang, D. Nat. Commun. 2013, 4, 2736
19. Xu, H.; Chen, X.; Gao, J.; Lin, J.; Addicoat, M.; Irle, S.; Jiang, D. Chem. Commun. 2014, 50, 1292-1294
20. Huang, N.; Chen, X.; Krishna, R.; Jiang, D. Angew. Chem., Int. Ed. 2015, 54, 2986-2990
21. Dogru, M.; Handloser, M.; Auras, F.; Kunz, T.; Medina, D.; Hartschuh, A.; Knochel, P.; Bein, T. Angew. Chem., Int. Ed. 2013, 52, 2920-2924
22. Calik, M.; Auras, F.; Salonen, L. M.; Bader, K.; Grill, I.; Handloser, M.; Medina, D. D.; Dogru, M.; Löbermann, F.; Trauner, D.; Hartschuh, A.; Bein, T. J. Am. Chem. Soc. 2014, 136, 17802-17807
23. Medina, D. D.; Rotter, J. M.; Hu, Y.; Dogru, M.; Werner, V.; Auras, F.; Markiewicz, J. T.; Knochel, P.; Bein, T. J. Am. Chem. Soc. 2015, 137, 1016-1019
24. Patwardhan, S.; Kocherzhenko, A. A.; Grozema, F. C.; Siebbeles, L. D. A. J. Phys. Chem. C 2011, 115, 11768-11772
25. Spitler, E. L.; Dichtel, W. R. Nat. Chem. 2010, 2, 672-677
26. Colson, J. W.; Woll, A. R.; Mukherjee, A.; Levendorf, M. P.; Spitler, E. L.; Shields, V. B.; Spencer, M. G.; Park, J.; Dichtel, W. R. Science 2011, 332, 228-231
27. Spitler, E. L.; Colson, J. W.; Uribe-Romo, F. J.; Woll, A. R.; Glovino, M. R.; Saldivar, A.; Dichtel, W. R. Angew. Chem., Int. Ed. 2012, 51, 2623-2627
28. Lukose, B.; Kuc, A.; Heine, T. Chem. -Eur. J. 2011, 17, 2388-2392
29. Kuhn, P.; Antonietti, M.; Thomas, A. Angew. Chem., Int. Ed. 2008, 47, 3450-3453
30. Campbell, N. L.; Clowes, R.; Ritchie, L. K.; Cooper, A. I. Chem. Mater. 2009, 21, 204-206
31. Berlanga, I.; Ruiz-González, M. L.; González-Calbet, J. M.; Fierro, J. L. G.; Mas-Ballesté, R.; Zamora, F. Small 2011, 7, 1207-1211
32. Li, W.; Yamamoto, Y.; Fukushima, T.; Saeki, A.; Seki, S.; Tagawa, S.; Masunaga, H.; Sasaki, S.; Takata, M.; Aida, T. J. Am. Chem. Soc. 2008, 130, 8886-8887
33. Kira, A.; Umeyama, T.; Matano, Y.; Yoshida, K.; Isoda, S.; Park, J. K.; Kim, D.; Imahori, H. J. Am. Chem. Soc. 2009, 131, 3198-3200
34. Hayashi, H.; Nihashi, W.; Umeyama, T.; Matano, Y.; Seki, S.; Shimizu, Y.; Imahori, H. J. Am. Chem. Soc. 2011, 130, 10736-10739
35. Tu, S.; Kim, S. H.; Joseph, J.; Modarell, D. A.; Parquette, J. R. J. Am. Chem. Soc. 2011, 133, 19125-19130
36. Ley, D.; Guzuman, C. X.; Adolfsson, K. H.; Scott, A. M.; Braunschweig, A. B. J. Am. Chem. Soc. 2014, 136, 7809-7812
37. Hartnett, R. E.; Dyar, S. M.; Margulies, E. A.; Shoer, L. E.; Cook, A. W.; Eaton, S. W.; Marks, T. J.; Wasielewski, M. R. Chem. Sci. 2015, 6, 402-411
38. Rao, K. V.; Haldar, R.; Kulkarni, C.; Maji, T. K.; Gerorge, S. J. Chem. Mater. 2012, 24, 969-971
39. Rao, K. V.; Mohapatra, S.; Maji, T. K.; Geroge, S. J. Chem. -Eur. J. 2012, 18, 4504-4509
40. Kasha, M.; Rawls, H. R.; Ashraf El-Bayoumi, M. Pure Appl. Chem. 1965, 11, 371-392
41. Ramamurthy, V.; Schanze, K. S. Organic and Inorganic Photochemistry; Marcel Dekker: New York, 1998.
42. Supur, M.; El-Khouly, M. E.; Seok, J. H.; Kay, K.-Y.; Fukuzumi, S. J. Phys. Chem. A 2011, 115, 14430-14437
43. In the previous report, we could observe the fast formation of the radical ion pair in the picosecond time scale when the solubility of the DZnPc-ANDI-COF was improved by delamination. In this case, the dispersion of the COFs was relatively low in many common organic solvents.
44. Herranz, M. A.; Ehli, C.; Campidelli, S.; Gutierrez, M.; Hug, G. L.; Ohkubo, K.; Fukuzumi, S.; Prato, M.; Martin, N.; Guldi, D. M. J. Am. Chem. Soc. 2008, 130, 66-73
45. Ohtani, M.; Fukuzumi, S. Chem. Commun. 2009, 4997-4999
46. Malig, J.; Jux, N.; Kiessling, D.; Cid, J. J.; Vazquez, P.; Torres, T.; Guldi, D. M. Angew. Chem., Int. Ed. 2011, 50, 3561-3565
47. The detector of our nanosecond laser system cannot detect the photoinduced events faster than 400 ns.
48. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265-322
49. Marcus, R. A. Pure Appl. Chem. 1997, 69, 13-29
50. Nkyokong, T.; Gasyma, Z.; Stillman, M. J. Inorg. Chem. 1987, 26, 548-553