Charge transfer or J-coupling? Assignment of an unexpected red-shifted absorption band in a naphthalenediimide-based metal-organic framework

Journal of Physical Chemistry Letters

Volumn 4, Issue 3, 2013, Pages 453-458

  McCarthy, Brian D ^a   Hontz, Eric R ^a   Yost, Shane R ^a   Van Voorhis, Troy ^a   Dincǎ, Mircea ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

charge transfer; constrained DFT; J coupling; Koopman's theorem; metal organic frameworks

Indexed keywords

CHARGE TRANSFER COMPLEX; CONSTRAINED DFT; J COUPLING; KOOPMAN'S THEOREM; LINEAR ARRANGEMENTS; METAL ORGANIC FRAMEWORK; OSCILLATOR STRENGTHS; PHOTOPHYSICAL MEASUREMENTS; RED-SHIFTED; TRANSITION DIPOLE MOMENTS;

CHARGE TRANSFER; CRYSTALLINE MATERIALS; DENSITY FUNCTIONAL THEORY; JAVA PROGRAMMING LANGUAGE;

LIGANDS;

EID: 84873416282     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz302076s     Document Type: Article

References (53)

1. Van Grondelle, R.; Dekker, J. P.; Gillbro, T.; Sundstrom, V. Energy Transfer and Trapping in Photosynthesis Biochim. Biophys. Acta 1994, 1187, 1-65 (Pubitemid 24262887)
2. Sener, M. K.; Olsen, J. D.; Hunter, C. N.; Schulten, K. Atomic-level Structural and Functional Model of a Bacterial Photosynthetic Membrane Vesicle Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 15723
3. Mcdermott, G.; Prince, S. M.; Freer, A. A.; Hawthornthwaite-Lawless, A. M.; Papiz, M. Z.; Cogdell, R. J.; Isaacs, N. W. Crystal-Structure of an Integral Membrane Light-Harvesting Complex from Photosynthetic Bacteria Nature 1995, 374, 517
4. Jiang, D. L.; Aida, T. Photoisomerization in Dendrimers by Harvesting of Low-Energy Photons Nature 1997, 388, 454
5. Mukhopadhyay, P.; Iwashita, Y.; Shirakawa, M.; Kawano, S.; Fujita, N.; Shinkai, S. Spontaneous Colorimetric Sensing of the Positional Isomers of Dihydroxynaphthalene in a 1D Organogel Matrix Angew. Chem., Int. Ed. 2006, 45, 1592
6. Ceroni, P.; Bergamini, G.; Marchioni, F.; Balzani, V. Luminescence As a Tool to Investigate Dendrimer Properties Prog. Polym. Sci. 2005, 30, 453
7. Bauer, R. E.; Grimsdale, A. C.; Mullen, K. Functionalised Polyphenylene Dendrimers and Their Applications Funct. Mol. Nanostruct. 2005, 245, 253
8. Chen, L.; Honsho, Y.; Seki, S.; Jiang, D. Light-Harvesting Conjugated Microporous Polymers: Rapid and Highly Efficient Flow of Light Energy with a Porous Polyphenylene Framework as Antenna J. Am. Chem. Soc. 2010, 132, 6742
9. Lin, V. S. Y.; Dimagno, S. G.; Therien, M. J. Highly Conjugated, Acetylenyl Bridged Porphyrins-New Models for Light-Harvesting Antenna Systems Science 1994, 264, 1105
10. Würthner, F.; Kaiser, T. E.; Saha-Möller, C. R. J-Aggregates: From Serendipitous Discovery to Supra-molecular Engineering of Functional Dye Materials Angew. Chem., Int. Ed. 2011, 50, 3376
11. Misawa, K.; Kobayashi, T. Hierarchical Structure in Oriented J-aggregates. In J-Aggregates; Kobayashi, T., Ed.; World Scientific Publishing: Singapore, 1996.
12. Kent, C. A.; Liu, D.; Ma, L.; Papanikolas, J. M.; Meyer, T. J.; Lin, W. Light Harvesting in Microscale Metal-Organic Frameworks by Energy Migration and Interfacial Electron Transfer Quenching J. Am. Chem. Soc. 2011, 133, 12940
13. Xie, Z.; Ma, L.; DeKrafft, K. E.; Jin, A.; Lin, W. Porous Phosphorescent Coordination Polymers for Oxygen Sensing J. Am. Chem. Soc. 2010, 132, 922
14. Lee, C. Y.; Farha, O. K.; Hong, B. J.; Sarjeant, A. a; Nguyen, S. T.; Hupp, J. T. Light-Harvesting Metal-Organic Frameworks (MOFs): Efficient Strut-to-Strut Energy Transfer in Bodipy and Porphyrin-Based MOFs J. Am. Chem. Soc. 2011, 133, 15858
15. Takashima, Y.; Martínez, V. M.; Furukawa, S.; Kondo, M.; Shimomura, S.; Uehara, H.; Nakahama, M.; Sugimoto, K.; Kitagawa, S. Molecular Decoding Using Luminescence from an Entangled Porous Framework Nat. Commun 2011, 2, 168
16. Perry, J. J., IV; Feng, P. L.; Meek, S. T.; Leong, K.; Doty, F. P.; Allendorf, M. D. Connecting Structure with Function in Metal-Organic Frameworks to Design Novel Photo- And Radioluminescent Materials J. Mater. Chem. 2012, 22, 10235
17. Feng, P. L.; Leong, K.; Allendorf, M. D. Charge-Transfer Interactions in Luminescent Mofs: Implications for Solid-State Temperature and Environmental Sensing Dalton Trans. 2012, 41, 8869
18. Shustova, N. B.; McCarthy, B. D.; Dincă, M. Turn-On Fluorescence in Tetraphenylethylene-Based Metal-Organic Frameworks: An Alternative to Aggregation-Induced Emission J. Am. Chem. Soc. 2011, 133, 20126
19. Wanderley, M. M.; Wang, C.; Wu, C.-D.; Lin, W. A Chiral Porous Metal-Organic Framework for Highly Sensitive and Enantioselective Fluorescence Sensing of Amino Alcohols J. Am. Chem. Soc. 2012, 134, 9050
20. Ma, B.-Q.; Mulfort, K. L.; Hupp, J. T. Microporous Pillared Paddle-Wheel Frameworks Based on Mixed-Ligand Coordination of Zinc Ions Inorg. Chem. 2005, 44, 4912
21. Würthner, F.; Ahmed, S.; Thalacker, C.; Debaerdemaeker, T. Core-Substituted Naphthalene Bisimides: New Fluorophors with Tunable Emission Wavelength for FRET Studies Chem.-Eur. J. 2002, 8, 4742
22. Bhosale, S. V; Jani, C. H.; Langford, S. J. Chemistry of Naphthalene Diimides Chem. Soc. Rev. 2008, 37, 331
23. Avinash, M. B.; Govindaraju, T. Engineering Molecular Organization of Naphthalenediimides: Large Nanosheets with Metallic Conductivity and Attoliter Containers Adv. Func. Mater. 2011, 21, 3875
24. Kumar, M.; George, S. J. Spectroscopic Probing of the Dynamic Self-Assembly of an Amphiphilic Naphthalene Diimide Exhibiting Reversible Vapochromism Chem.-Eur. J. 2011, 17, 11102
25. Molla, M. R.; Ghosh, S. Structural Variations on Self-Assembly and Macroscopic Properties of 1,4,5,8-Naphthalene-diimide Chromophores Chem. Mater. 2011, 23, 95
26. Shao, H.; Parquette, J. R. Self-Assembly of 1-D n-Type Nanostructures Based on Naphthalene Diimide-Appended Dipeptides Chem. Commun. 2012, 46, 4285
27. Busby, M.; Blum, C.; Tibben, M.; Fibikar, S.; Calzaferri, G.; Subramaniam, V.; De Cola, L. Time, Space, and Spectrally Resolved Studies on J-Aggregate Interactions in Zeolite L Nanochannels J. Am. Chem. Soc. 2008, 130, 10970
28. Usov, P. M.; Fabian, C.; D'Alessandro, D. M. Rapid Determination of the Optical and Redox Properties of a Metal-Organic Framework via in Situ Solid State Spectroelectrochemistry Chem. Commun. 2012, 48, 3945
29. Pan, M.; Lin, X.-M.; Li, G.-B.; Su, C.-Y. Progress in the Study of Metal-organic Materials Applying Naphthalene Diimide (NDI) Ligands Coord. Chem. Rev. 2011, 255, 1921
30. Shao, H.; Nguyen, T.; Romano, N. C.; Modarelli, D. a; Parquette, J. R. Self-Assembly of 1-D n-Type Nanostructures Based on Naphthalene Diimide-Appended Dipeptides J. Am. Chem. Soc. 2009, 131, 16374
31. Busby, M.; Devaux, A.; Blum, C.; Subramaniam, V.; Calzaferri, G.; De Cola, L. Interactions of Perylene Bisimide in the One-Dimensional Channels of Zeolite L J. Phys. Chem. C 2011, 115, 5974
32. Martínez-Martínez, V.; Furukawa, S.; Takashima, Y.; López Arbeloa, I.; Kitagawa, S. Charge Transfer and Exciplex Emissions from a Naphthalenediimide-Entangled Coordination Framework Accommodating Various Aromatic Guests J. Phys. Chem. C 2012, 116, 26084
33. Trivedi, D. R.; Fujiki, Y.; Goto, Y.; Fujita, N.; Shinkai, S.; Sada, K. A Naked-Eye Colorimetric Indicator to Discriminate Aromatic Compounds by Solid-State Charge-Transfer Complexation Chem. Lett. 2008, 37, 550
34. Takashima, Y.; Furukawa, S.; Kitagawa, S. Control of the Charge-Transfer Interaction between a Flexible Porous Coordination Host and Aromatic Guests by Framework Isomerism CrystEngComm 2011, 13, 3360
35. n Inorg. Chem. Commun. 2009, 12, 994
36. Ye, Q.; Song, Y.-M.; Wang, G.-X.; Chen, K.; Fu, D.-W.; Chan, P. W. H.; Zhu, J.-S.; Huang, S. D.; Xiong, R.-G. Ferroelectric Metal-Organic Framework with a High Dielectric Constant J. Am. Chem. Soc. 2006, 128, 6554
37. Fu, D.-W.; Ye, H.-Y.; Ye, Q.; Pan, K.-J.; Xiong, R.-G. Ferroelectric Metal-Organic Coordination Polymer with a High Dielectric Constant Dalton Trans. 2008, 874
38. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer: New York, 2006.
39. Furukawa, S.; Hirai, K.; Takashima, Y.; Nakagawa, K.; Kondo, M.; Tsuruoka, T.; Sakata, O.; Kitagawa, S. A Block PCP Crystal: Anisotropic Hybridization of Porous Coordination Polymers by Face-Selective Epitaxial Growth Chem. Commun. 2009, 5097
40. Han, L.; Qin, L.; Xu, L.; Zhou, Y.; Sun, J.; Zou, X. a Novel Photochromic Calcium-Based Metal-Organic Framework Derived from a Naphthalene Diimide Chromophore Chem. Commun. 2012, 704, 406
41. Autschbach, J. Charge-Transfer Excitations and Time-Dependent Density Functional Theory: Problems and Some Proposed Solutions ChemPhysChem 2009, 10, 1757
42. Tawada, Y.; Tsuneda, T.; Yanagisawa, S.; Yanai, T.; Hirao, K. a Long-Range-Corrected Time-Dependent Density Functional Theory J. Chem. Phys. 2004, 120, 8425
43. Runge, E.; Gross, E. K. E. Density-Functional Theory for Time-Dependent Systems Phys. Rev. Lett. 1984, 52, 997
44. Iikura, H.; Tsuneda, T.; Yanai, T.; Hirao, K. A Long-Range Correction Scheme for Generalized-Gradient-Approximation Exchange Functionals J. Chem. Phys. 2001, 115, 3540
45. Rohrdanz, M. A.; Martins, K. M.; Herbert, J. M. a Long-Range-Corrected Density Functional That Performs Well for Both Ground-State Properties and Time-Dependent Density Functional Theory Excitation Energies, Including Charge-Transfer Excited States J. Chem. Phys. 2009, 130, 054112
46. Livshits, E.; Baer, R. a Well-Tempered Density Functional Theory of Electrons in Molecules Phys. Chem. Chem. Phys. 2007, 9, 2932
47. Refaely-Abramson, S.; Baer, R.; Kronik, L. Fundamental and Excitation Gaps in Molecules of Relevance for Organic Photovoltaics from an Optimally Tuned Range-Separated Hybrid Functional Phys. Rev. B 2011, 84, 075144
48. Baer, R.; Neuhauser, D. Density Functional Theory with Correct Long-Range Asymptotic Behavior Phys. Rev. Lett. 2005, 94, 043002
49. Baer, R.; Livshits, E.; Neuhauser, D. Avoiding Self-Repulsion in Density Functional Description of Biased Molecular Junctions Chem. Phys. 2006, 329, 266
50. Wu, Q.; Van Voorhis, T. Direct Optimization Method to Study Constrained Systems within Density-Functional theory Phys. Rev. A 2005, 72, 024502
51. Tomasi, J.; Persico, M. Molecular Interactions in Solution: An Overview of Methods Based on Continuous Distributions of the Solvent Chem. Rev. 1994, 94, 2027
52. Wu, Q.; Cheng, C.-L.; Van Voorhis, T. Configuration Interaction Based on Constrained Density Functional Theory: A Multireference Method J. Chem. Phys. 2007, 127, 164119
53. Kong, J.; White, C. A.; Krylov, A. I.; Adamson, R. D.; Furlani, T. R.; Lee, S.; Lee, A. M.; Gwaltney, S. R.; Adams, T. R.; Ochsenfeld, C. Q-Chem 2.0: A High-Performance Ab Initio Electronic Structure Program Package J. Comput. Chem. 2000, 21, 1532