Nanostructured donor-acceptor self assembly with improved photoconductivity

ACS Applied Materials and Interfaces

Volumn 6, Issue 21, 2014, Pages 19434-19448

  Saibal, B ^a,b   Ashar, A Z ^d   Devi, R Nandini ^a,b   Narayan, K S ^d   Asha, S K ^a,b,c  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

^c NATIONAL CHEMICAL LABORATORY   (India)

^d JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

donor acceptor; hydrogen bonding; oligo(p phenylenevinylene); perylenebisimide; photoconductivity; supramolecular polymeric nanostructures

Indexed keywords

AGGREGATES; AROMATIC COMPOUNDS; HYDROGEN BONDS; LAMELLAR STRUCTURES; MOLECULES; MORPHOLOGY; NANOSTRUCTURES; PHOTOCONDUCTIVITY; POLYMERIZATION; RED SHIFT; SPONTANEOUS EMISSION; SUPRAMOLECULAR CHEMISTRY; THIN FILMS;

DONOR ACCEPTORS; FLUORESCENCE EMISSION; OLIGO(P-PHENYLENEVINYLENE); PERYLENEBISIMIDE; SPACE-CHARGE-LIMITED CURRENT; SUPRAMOLECULAR COMPLEXES; SUPRAMOLECULAR POLYMERS; WIDE-ANGLE X-RAY DIFFRACTION;

SELF ASSEMBLY;

EID: 84910155401     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am5055542     Document Type: Article

References (44)

1. Aida, T.; Meijer, E. W.; Stupp, S. I. Functional Supramolecular Polymers Science 2012, 335, 813-817
2. Neuteboom, E. E.; Meskers, S. C. J.; Van Hal, P. A.; Van Duren, J. K. J.; Meijer, E. W.; Janssen, R. A. J.; Dupin, H.; Pourtois, G.; Cornil, J.; Lazzaroni, R.; Brédas, J.-L.; Beljonne, D. Alternating Oligo(p -phenylene vinylene)-Perylene Bisimide Copolymers: Synthesis, Photophysics, and Photovoltaic Properties of a New Class of Donor-Acceptor Materials J. Am. Chem. Soc. 2003, 125, 5174-5176
3. Jalani, K.; Kumar, M.; George, S. J. Mixed Donor-Acceptor Charge-Transfer Stacks Formed via Hierarchical Self-Assembly of a Non-Covalent Amphiphilic Foldamer Chem. Commun. 2013, 49, 14968-14969
4. 60-terminated Self-Assembled Monolayer Adv. Mater. 2013, 25, 6453-6458
5. Aiyar, A. R.; Hong, Jung-Il.; Izumi, J.; Choi, D.; Kleinhenz, N.; Reichmanis, E. Ultrasound-Induced Ordering in Poly(3-hexylthiophene): Role of Molecular and Process Parameters on Morphology and Charge Transport ACS Appl. Mater. Interfaces 2013, 5, 2368-2377
6. De Boer, B.; Stalmach, U.; van Hutten, P. F.; Melzer, C.; Krasnikov, V. K.; Hadziioannou, G. Supramolecular Self-Assembly and Opto-Electronic Properties of Semiconducting Block Copolymers Polymer 2001, 42, 9097-9109
7. Mativetsky, J. M.; Kastler, M.; Savage, R. C.; Gentilini, D.; Palma, M.; Pisula, W.; Müllen, K.; Samorí, P. Self-Assembly of a Donor-Acceptor Dyad Across Multiple Length Scales: Functional Architectures for Organic Electronics Adv. Funct. Mater. 2009, 19, 2486-2494
8. Zapala, J.; Knor, M.; Jaroch, T.; Maranda-Niedbala, A.; Kurach, E.; Kotwica, K.; Nowakowski, R.; Djurado, D.; Pecaut, J.; Zagorska, M.; Pron, A. Self-Assembly Properties of Semiconducting Donor-Acceptor-Donor Bithienyl Derivatives of Tetrazine and Thiadiazole-Effect of the Electron Accepting Central Ring Langmuir 2013, 29, 14503-14511
9. Ikkala, O.; ten Brinke, G. Functional Materials Based on Self-Assembly of Polymeric Supramolecules Science 2002, 295, 2407-2409
10. Hanski, S.; Houbenov, N.; Ruokolainen, J.; Chondronicola, D.; Iatrou, H.; Hadjichristidis, N.; Ikkala, O. Hierarchical Ionic Self-Assembly of Rod-Comb Block Copolypeptide-Surfactant Complexes Biomacromolecules 2006, 7, 3379-3384
11. Ruokolainen, J.; Mäkinen, R.; Torkkeli, M.; Mäkelä, T.; Serimaa, R.; ten Brinke, G.; Ikkala, O. Switching Supramolecular Polymeric Materials with Multiple Length Scales Science 1998, 280, 557-560
12. Ruokolainen, J.; ten Brinke, G.; Ikkala, O.; Torkkeli, M.; Serimaa, R.; Komanschek, E. Order-Disorder Transitions in Polymer-Surfactant Systems Phys. Rev. E 1996, 54, 6646-6649
13. Narayan, R.; Kumar, P.; Narayan, K. S.; Asha, S. K. Nanostructured Crystalline Comb Polymer of Perylenebisimide by Directed Self-Assembly: Poly(4-vinylpyridine)-pentadecylphenol Perylenebisimide Adv. Funct. Mater. 2013, 23, 2033-2043
14. Rancatore, B. J.; Mauldin, C. E.; Fréchet, J. M. J.; Xu, T. Small Molecule-Guided Thermoresponsive Supramolecular Assemblies Macromolecules 2012, 45, 8292-8299
15. Rancatore, B. J.; Mauldin, C. E.; Tung, S. H.; Wang, C.; Hexemer, A.; Strzalka, J.; Fréchet, J. M.J.; Xu, T. Nanostructured Organic Semiconductors via Directed Supramolecular Assembly ACS Nano 2010, 4, 2721-2729
16. Perepichka, I. I.; Lu, Q.; Badia, A.; Bazuin, C. G. Understanding and Controlling Morphology Formation in Langmuir-Blodgett Block Copolymer Films Using PS-P4VP and PS- P4VP/PDP Langmuir 2013, 29, 4502-4519 29, 4502-4519
17. Hu, H.; Gopinadhan, M.; Osuji, C. O. Directed Self-Assembly of Block Copolymers: A Tutorial Review of Strategies for Enabling Nanotechnology with Soft Matter 2014, 10, 3867-3889
18. Cummins, C.; Borah, D.; Rasappa, S.; Chaudhari, A.; Ghoshal, T.; O'Driscoll, B. M. D.; Carolan, P.; Petkov, N.; Holmes, J. D.; Morris, M. A. Self-Assembly of Polystyrene- block -Poly(4-vinylpyridine) Block Copolymer on Molecularly Functionalized Silicon Substrates: Fabrication of Inorganic Nanostructured Etchmask for Lithographic Use J. Mater. Chem. C 2013, 1, 7941-7951
19. Kao, J.; Thorkelsson, K.; Bai, P.; Rancatore, B. J.; Xu, T. Toward Functional Nanocomposites: Taking the Best of Nanoparticles, Polymers, and Small Molecules Chem. Soc. Rev. 2013, 42, 2654-2678
20. Thorkelsson, K.; Mastroianni, A. J.; Ercius, P.; Xu, T. Direct Nanorod Assembly Using Block Copolymer-Based Supramolecules Nano Lett. 2012, 12, 498-504
21. Ruokolainen, J.; ten Brinke, G.; Ikkala, O. Supramolecular Polymeric Materials with Hierarchical Structure-Within-Structure Morphologies Adv. Mater. 1999, 11, 777-780
22. van Zoelen, W.; van Ekenstein, G. A.; Polushkin, E.; Ikkala, O.; ten Brinke, G. Nanorod Engineering by Reinforcing Hexagonally Self-Assembled PS- b -P4VP(DDP) with PPE Soft Matter 2005, 1, 280-283
23. Ono, R. J.; Todd, A. D.; Hu, Z.; Vanden Bout, D. A.; Bielawski, C. W. Synthesis of a Donor-Acceptor Diblock Copolymer via Two Mechanistically Distinct, Sequential Polymerizations Using a Single Catalyst Macromol. Rapid Commun. 2014, 35, 204-209
24. Wang, J.; Higashihara, T. Synthesis of All-Conjugated Donor-Acceptor Block Copolymers and Their Application in All-Polymer Solar Cells Polym. Chem. 2013, 4, 5518-5526
25. You, C.-C.; Würthner, F. Self-Assembly of Ferrocene-Functionalized Perylene Bisimide Bridging Ligands with Pt(II) Corner to Electrochemically Active Molecular Squares J. Am. Chem. Soc. 2003, 125, 9716-9725
26. Lane, T. J.; Nakagawa, I.; Walter, J. L.; Kandathil, A. J. Infrared Investigation of Certain Imidazole Derivatives and Their Metal Chelates Inorg. Chem. 1962, 1, 267-276
27. Moussa, K.; Decker, C. Light-Induced Polymerization of New Highly Reactive Acrylic Monomers J. Polym. Sci. Part A: Polym. Chem. 1993, 31, 2197-2203
28. Rekha, N.; Asha, S. K. Synthesis and FTIR Spectroscopic Investigation of the UV Curing Kinetics of Telechelic Urethane Methacrylate Crosslinkers Based on the Renewable Resource-Cardanol J. Appl. Polym. Sci. 2008, 109, 2781-2790
29. Schenning, A. P. H. J.; Peeters, E.; Meijer, E. W. Energy Transfer in Supramolecular Assemblies of Oligo(p -phenylene vinylene)s Terminated Poly(propylene imine) Dendrimers J. Am. Chem. Soc. 2000, 122, 4489-4495
30. Shao, C.; Grüne, M.; Stolte, M.; Würthner, F. Perylene Bisimide Dimer Aggregates: Fundamental Insights into Self-Assembly by NMR and UV/Vis Spectroscopy Chem.-Eur. J. 2012, 18, 13665-13677
31. Draper, E. R.; Walsh, J. J.; McDonald, T. O.; Zwijnenburg, M. A.; Cameron, P. J.; Cowan, A. J.; Adams, D. J. Air-Stable Photoconductive Films Formed From Perylene Bisimide Gelators J. Mater. Chem. C 2014, 2, 5570-5575
32. Chen, Z.; Stepanenko, V.; Dehm, V.; Prins, P.; Siebbeles, L. D. A.; Seibt, J.; Marquetand, P.; Engel, V.; Würthner, F. Photoluminescence and Conductivity of Self-Assembled π-π Stacks of Perylene Bisimide Dyes Chem.-Eur. J. 2007, 13, 436-449
33. Zhang, J.; Hoeben, F. J. M.; Pouderoijen, M. J.; Schenning, A. P.; Meijer, E. W.; De Schryver, F. C.; De Feyter, S. Hydrogen-Bonded Oligo(p -phenylene vinylene) Functionalized with Perylene Bisimide: Self-Assembly and Energy Transfer Chem.-Eur. J. 2006, 12, 9046-9055
34. van Hutten, P. F.; Brouwer, H.-J.; Krasnikov, V. V.; Ouali, L.; Stalmach, U.; Hadziioannou, G. Effect of Solid-State Structure on Optical Properties of Conjugated Organic Materials Synth. Met. 1999, 102, 1443-1446
35. Ramakrishna Matte, H. S. S.; Jain, A.; George, S. J. Covalently Linked Graphene-Oligo(phenylene vinylene) Adduct: Self Organization and Photo-physical Properties RSC Adv. 2012, 2, 6290-6294
36. Samuel, I. D.W.; Rumbles, G.; Collison, C. Efficient Interchain Photoluminescence in a High-Electron-Affinity Conjugated Polymer Phys. Rev. B 1995, 52, RII 573-RII 576
37. George, S. J.; Ajayaghosh, A. Self-Assembled Nanotapes of Oligo(p -phenylene vinylene)s: Sol-Gel-Controlled Optical Properties in Fluorescent π-Electronic Gels Chem.-Eur. J. 2005, 11, 3217-3227
38. Hutten, P. F. V.; Krasnikov, V. V.; Hadziioannou, G. A. Model Oligomer Approach to Light-Emitting Semiconducting Polymers Acc. Chem. Res. 1999, 32, 257-265
39. Brochon, C.; Sary, N.; Mezzenga, R.; Ngov, C.; Richard, F.; May, M.; Hadziioannou, G. Synthesis of Poly(p -phenylene vinylene)-Polystyrene-Based Rod-Coil Block Copolymer by Atom Transfer Radical Polymerization: Toward a Self-Organized Lamellar Semiconducting Material J. Appl. Polym. Sci. 2008, 110, 3664-3670
40. De Luca, G.; Liscio, A.; Battagliarin, G.; Chen, L.; Scolaro, L. M.; Müllen, K.; Samorì, P.; Palermo, V. Orthogonal Self-Assembly and Selective Solvent Vapour Annealing: Simplified Processing of a Photovoltaic Blend Chem. Commun. 2013, 49, 4322-4324
41. Ciesielski, A.; Szabelski, P.; Cadeddu, A.; Cook, T. R.; Stang, P. J.; Samorì, P. Concentration-Dependent Supramolecular Engineering of Hydrogen-Bonded Nanostructures at Surfaces: Predicting Self-Assembly in 2D J. Am. Chem. Soc. 2013, 135, 6942-6950
42. Schenning, A. P. H. J.; van Herrikhuyzen, J.; Jonkheijm, P.; Chen, Z.; Würthner, F.; Meijer, E. W. Photoinduced Electron Transfer in Hydrogen-Bonded Oligo(p -phenylene vinylene)-Perylene Bisimide Chiral Assemblies J. Am. Chem. Soc. 2002, 124, 10252-10253
43. Würthner, F.; Chen, Z.; Hoeben, F. J. M.; Osswald, P.; You, C.-C.; Jonkheijm, P.; van Herrikhuyzen, J.; Schenning, A. P. H. J.; Schoot, P. P. A. M. v. d.; Meijer, E. W.; Beckers, E. H. A.; Meskers, S. C. J.; Janssen, R. A. J. Supramolecular p-n Heterojunctions by Co-Self-Organization of Oligo(p -phenylene vinylene) and Perylene Bisimide Dyes J. Am. Chem. Soc. 2004, 126, 10611-10618
44. Pascal, J.; Stutzmann, N.; Chen, Z.; de Leeuw, D. M.; Meijer, E. W.; Schenning, A. P. H. J.; Würthner, F. Control of Ambipolar Thin Film Architectures by Co-Self-Assembling Oligo(p -phenylene vinylene)s and Perylene Bisimides J. Am. Chem. Soc. 2006, 128, 9535-9540