logo

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Chem. Mater. 2008, 20, 24, 7492-7500
RETURN TO ISSUEPREVArticleNEXT

Photoconductivity of Porphyrin Nanochannels Composed of Diprotonated Porphyrin Dications with Saddle Distortion and Electron Donors

View Author Information
Department of Material and Life Science, Graduate School of Engineering, Osaka University and SORST (JST), Suita, Osaka 565-0871, Japan, and School of Materials Science, Japan Advanced Institute of Science and Technology (JAIST) and PRESTO, JST, Nomi, Ishikawa 923-1292, Japan
* Correspding authors: [email protected] (T.K.) and [email protected] (S.F.).
†Osaka University and SORST (JST).
‡JAIST and PRESTO, JST.
§Present address: Department of Applied Chemistry, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan.
Cite this: Chem. Mater. 2008, 20, 24, 7492–7500
Publication Date (Web):November 20, 2008
https://doi.org/10.1021/cm802460t
Copyright © 2008 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
1558
Altmetric
-
Citations
41
LEARN ABOUT THESE METRICS

Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.

Read OnlinePDF (1 MB)
Get e-Alerts
Supporting Info (2)»
SUBJECTS:

Abstract

Abstract Image

Supramolecular architecture named as porphyrin nanochannels (PNCs), including tetrathiafulvalene (TTF) and p-aminophenol as electron-donating guests in the inner space, was prepared with the hydrochloride salt of dodecaphenylporphyrin ([H4DPP]Cl2) by self-assembly based on intermolecular π−π interactions. The crystal structure of the TTF-included PNC (PNC−TTF) was determined by X-ray crystallography. Intermolecular π−π interaction was recognized among peripheral phenyl groups of the porphyrin, mainly in the direction of the crystallographic c axis to form a column structure. Photoinduced electron transfer from the guest molecules to [H4DPP]Cl2 occurred to give the electron-transfer state involving cation radicals of the guest molecules and one-electron reduced [H4DPP]Cl2, {[H4DPP+•]Cl2}−, via the photoexcited singlet state of [H4DPP]Cl2 in PNC. The reactions were examined by solid-state femtosecond laser flash photolysis and ESR measurements to determine the rate constants of electron transfer and electronic structures of the cation radicals included in the cavity, respectively. A single crystal (0.87 × 0.23 × 0.10 mm3) of PNC−TTF exhibited photoconductivity upon photoirradiation at 633 nm with a He−Ne laser (5 mW), and the photocurrent was 0.7 nA at electrical field strength of 3.5 × 104 V cm−1. The photocurrent showed direction dependence toward the crystallographic c axis. This indicates that the intermolecular π−π interaction is the main conduction pathway. Various PNC supramolecules including TTF and other electron-donating guest molecules were also employed to construct photoelectrochemical cells with use of SnO2 transparent electrodes. Short-circuit photocurrent measurements were made on the cells with the OTE/SnO2/PNC−guest photoanodes, and they exhibited clear photoresponse upon photoirradiation. The photocurrents increase with increasing the rate constants of the photoinduced electron transfer from the guest molecules to [H4DPP]Cl2, exhibiting saturation behavior. The performance of the cell with the OTE/SnO2/PNC−TTF electrode exhibited the maximum IPCE (incident photon-to-current efficiency) value of 10.1% at 460 nm, which corresponded to the absorption maximum of the Soret band of [H4DPP]Cl2 on the electrode.

Supporting Information

ARTICLE SECTIONS
Jump To

Crystallorgaphic data for PNC−TTF (CIF format), solid-state fluorescence spectra of PNC−water and PNC−TTF, transient absorption spectra and time profile for PNC−(p-AP), and the full list of authors for ref 30 (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 43 publications.

  1. Jing Xu, Li-Jun Xue, Jin-Le Hou, Zhong-Nan Yin, Xuan Zhang, Qin-Yu Zhu, and Jie Dai . A Strong Donor–Acceptor System Based on a Metal Chalcogenide Cluster and Porphyrin. Inorganic Chemistry 2017, 56 (14) , 8036-8044. https://doi.org/10.1021/acs.inorgchem.7b00775
  2. Atanu Jana, Masatoshi Ishida, Jung Su Park, Steffen Bähring, Jan O. Jeppesen, and Jonathan L. Sessler . Tetrathiafulvalene- (TTF-) Derived Oligopyrrolic Macrocycles. Chemical Reviews 2017, 117 (4) , 2641-2710. https://doi.org/10.1021/acs.chemrev.6b00375
  3. Bettina Wagner, Natalie Dehnhardt, Martin Schmid, Benedikt P. Klein, Lukas Ruppenthal, Philipp Müller, Malte Zugermeier, J. Michael Gottfried, Sina Lippert, Marc-Uwe Halbich, Arash Rahimi-Iman, and Johanna Heine . Color Change Effect in an Organic–Inorganic Hybrid Material Based on a Porphyrin Diacid. The Journal of Physical Chemistry C 2016, 120 (49) , 28363-28373. https://doi.org/10.1021/acs.jpcc.6b11188
  4. Pengchong Xue, Panpan Wang, Boqi Yao, Jiabao Sun, Peng Gong, Zhenqi Zhang, Chong Qian, and Ran Lu . Nanofibers of Hydrogen-Bonded Two-Component Gel with Closely Connected p- and n-Channels and Photoinduced Electron Transfer. ACS Applied Materials & Interfaces 2014, 6 (23) , 21426-21434. https://doi.org/10.1021/am506422m
  5. Yong-Gang Sun, Shu-Fang Ji, Peng Huo, Jing-Xue Yin, Yu-De Huang, Qin-Yu Zhu, and Jie Dai . Role of the Coordination Center in Photocurrent Behavior of a Tetrathiafulvalene and Metal Complex Dyad. Inorganic Chemistry 2014, 53 (6) , 3078-3087. https://doi.org/10.1021/ic402993y
  6. Taku Hasobe . Porphyrin-Based Supramolecular Nanoarchitectures for Solar Energy Conversion. The Journal of Physical Chemistry Letters 2013, 4 (11) , 1771-1780. https://doi.org/10.1021/jz4005152
  7. Jagannath Bhuyan and Sabyasachi Sarkar . Self-Assembly of Magnesium and Zinc Trimethoxyphenylporphyrin Polymer as Nanospheres and Nanorods. Crystal Growth & Design 2011, 11 (12) , 5410-5414. https://doi.org/10.1021/cg2010002
  8. Kazuo Tanaka, Fumiyasu Ishiguro and Yoshiki Chujo. Facile Preparation of Concentration-Gradient Materials with Radical Spin of the Mixed-Valence Tetrathiafulvalene in Conventional Polymer Films. Langmuir 2010, 26 (12) , 10254-10258. https://doi.org/10.1021/la100431k
  9. Kazuo Tanaka, Fumiyasu Ishiguro and Yoshiki Chujo. Photoinduced Radical Generation and Self-Assembly of Tetrathiafulvalene into the Mixed-Valence State in the Poly(vinyl chloride) Film under UV Irradiation. Langmuir 2010, 26 (2) , 1152-1156. https://doi.org/10.1021/la902246z
  10. Hirofumi Nobukuni, Fumito Tani, Yuichi Shimazaki, Yoshinori Naruta, Kei Ohkubo, Tatsuaki Nakanishi, Takahiko Kojima, Shunichi Fukuzumi and Shu Seki. Anisotropic High Electron Mobility and Photodynamics of a Self-Assembled Porphyrin Nanotube Including C60 Molecules. The Journal of Physical Chemistry C 2009, 113 (45) , 19694-19699. https://doi.org/10.1021/jp9076849
  11. Atula S. D. Sandanayaka, Tatsuya Murakami and Taku Hasobe . Preparation and Photophysical and Photoelectrochemical Properties of Supramolecular Porphyrin Nanorods Structurally Controlled by Encapsulated Fullerene Derivatives. The Journal of Physical Chemistry C 2009, 113 (42) , 18369-18378. https://doi.org/10.1021/jp9063577
  12. Yu Wang, Shuxin Cui, Bo Li, Jingping Zhang and Yan Zhang . Synthesis and Characterization of Monosubstituted TTF and Its Solvent Dependent Mono- and Dication Charge-Transfer Salts. Crystal Growth & Design 2009, 9 (9) , 3855-3858. https://doi.org/10.1021/cg900635f
  13. Chandrabhan Verma, Eno E. Ebenso, M.A. Quraishi. Transition metal nanoparticles in ionic liquids: Synthesis and stabilization. Journal of Molecular Liquids 2019, 276 , 826-849. https://doi.org/10.1016/j.molliq.2018.12.063
  14. Marc Kielmann, Mathias O. Senge. Molekulares Engineering freier Porphyrinbasen als Liganden - das N-H⋅⋅⋅X-Bindungsmotiv in Tetrapyrrolen. Angewandte Chemie 2019, 131 (2) , 424-448. https://doi.org/10.1002/ange.201806281
  15. Marc Kielmann, Mathias O. Senge. Molecular Engineering of Free-Base Porphyrins as Ligands-The N−H⋅⋅⋅X Binding Motif in Tetrapyrroles. Angewandte Chemie International Edition 2019, 58 (2) , 418-441. https://doi.org/10.1002/anie.201806281
  16. Wataru Suzuki, Hiroaki Kotani, Tomoya Ishizuka, Kei Ohkubo, Yoshihito Shiota, Kazunari Yoshizawa, Shunichi Fukuzumi, Takahiko Kojima. Thermodynamics and Photodynamics of a Monoprotonated Porphyrin Directly Stabilized by Hydrogen Bonding with Polar Protic Solvents. Chemistry - A European Journal 2017, 23 (19) , 4669-4679. https://doi.org/10.1002/chem.201606012
  17. Karishma Devi Borah, Jagannath Bhuyan. Magnesium porphyrins with relevance to chlorophylls. Dalton Transactions 2017, 46 (20) , 6497-6509. https://doi.org/10.1039/C7DT00823F
  18. Li-Jun Xue, Peng Huo, Yan-Hong Li, Jin-Le Hou, Qin-Yu Zhu, Jie Dai. An ionic charge-transfer dyad prepared cost-effectively from a tetrathiafulvalene carboxylate anion and a TMPyP cation. Physical Chemistry Chemical Physics 2016, 18 (4) , 2940-2948. https://doi.org/10.1039/C5CP06141E
  19. Takao Sakuma, Hayato Sakai, Yasuyuki Araki, Takehiko Wada, Taku Hasobe. Control of local structures and photophysical properties of zinc porphyrin-based supramolecular assemblies structurally organized by regioselective ligand coordination. Physical Chemistry Chemical Physics 2016, 18 (7) , 5453-5463. https://doi.org/10.1039/C5CP07110K
  20. Jing-Xue Yin, Peng Huo, Sheng Wang, Jing Wu, Qin-Yu Zhu, Jie Dai. A tetrathiafulvalene-grafted titanium-oxo-cluster material: self-catalyzed crystal exfoliation and photocurrent response properties. Journal of Materials Chemistry C 2015, 3 (2) , 409-415. https://doi.org/10.1039/C4TC02009J
  21. Hayato Sakai, Takuya Kamimura, Fumito Tani, Taku Hasobe. Supramolecular photovoltaic cells utilizing inclusion complexes composed of Li + @ C 60 and cyclic porphyrin dimer. Journal of Porphyrins and Phthalocyanines 2015, 19 (01-03) , 242-250. https://doi.org/10.1142/S1088424614501156
  22. Takahiko Kojima, Ryosuke Kobayashi, Tomoya Ishizuka, Shinya Yamakawa, Hiroaki Kotani, Tatsuaki Nakanishi, Kei Ohkubo, Yoshihito Shiota, Kazunari Yoshizawa, Shunichi Fukuzumi. Binding of Scandium Ions to Metalloporphyrin-Flavin Complexes for Long-Lived Charge Separation. Chemistry - A European Journal 2014, 20 (47) , 15518-15532. https://doi.org/10.1002/chem.201403960
  23. Sunao Hirayama, Hayato Sakai, Yasuyuki Araki, Minako Tanaka, Masaki Imakawa, Takehiko Wada, Taishi Takenobu, Taku Hasobe. Systematic Control of the Excited-State Dynamics and Carrier-Transport Properties of Functionalized Benzo[ ghi ]perylene and Coronene Derivatives. Chemistry - A European Journal 2014, 371 , n/a-n/a. https://doi.org/10.1002/chem.201304679
  24. Y. Kalachyova, O. Lyutakov, V. Prajzler, J. Tuma, J. Siegel, V. Švorčík. Porphyrin migration and aggregation in a poly(methylmethacrylate) matrix. Polymer Composites 2014, 35 (4) , 665-670. https://doi.org/10.1002/pc.22709
  25. Yuanyuan Fang, P. Bhyrappa, Zhongping Ou, Karl M. Kadish. Planar and Nonplanar Free-Base Tetraarylporphyrins: β-Pyrrole Substituents and Geometric Effects on Electrochemistry, Spectroelectrochemistry, and Protonation/Deprotonation Reactions in Nonaqueous Media. Chemistry - A European Journal 2014, 20 (2) , 524-532. https://doi.org/10.1002/chem.201303141
  26. Di Gao, Gabriel Canard, Michel Giorgi, Pierre Vanloot, Teodor Silviu Balaban. Electronic and Steric Effects of the Peripheral Substitution in Deca- and Undecaaryl Metallocorroles. European Journal of Inorganic Chemistry 2014, 2014 (2) , 279-287. https://doi.org/10.1002/ejic.201301314
  27. Shunichi Fukuzumi, Takahiko Kojima. Nanostructures and Electron-Transfer Functions of Nonplanar Porphyrins. 2013,,, 131-146. https://doi.org/10.1002/9781118354377.ch6
  28. , . Organic Nanomaterials. 2013,,https://doi.org/10.1002/9781118354377
  29. Tomoya Ishizuka, Muniappan Sankar, Takahiko Kojima. Control of the spatial arrangements of supramolecular networks based on saddle-distorted porphyrins by intermolecular hydrogen bonding. Dalton Transactions 2013, 42 (45) , 16073. https://doi.org/10.1039/c3dt51467f
  30. Shunichi Fukuzumi, Kei Ohkubo. Long-lived photoinduced charge separation for solar cell applications in supramolecular complexes of multi-metalloporphyrins and fullerenes. Dalton Transactions 2013, 42 (45) , 15846. https://doi.org/10.1039/c3dt51883c
  31. Shunichi Fukuzumi, Tatsuhiko Honda, Takahiko Kojima. Structures and photoinduced electron transfer of protonated complexes of porphyrins and metallophthalocyanines. Coordination Chemistry Reviews 2012, 256 (21-22) , 2488-2502. https://doi.org/10.1016/j.ccr.2012.01.011
  32. Luis Aparici Plaza, Jaroslaw Chojnacki. Influence of chloroform on crystalline products yielded in reactions of 5,10,15,20-tetraphenylporphyrin with HCl and copper(II) salts. Acta Crystallographica Section C Crystal Structure Communications 2012, 68 (1) , m24-m28. https://doi.org/10.1107/S0108270111054102
  33. Tomoya Ishizuka, Muniappan Sankar, Yusuke Yamada, Shunichi Fukuzumi, Takahiko Kojima. Porphyrin nanochannels reinforced by hydrogen bonding. Chemical Communications 2012, 48 (52) , 6481. https://doi.org/10.1039/c2cc31142a
  34. Taku Hasobe. Photo- and electro-functional self-assembled architectures of porphyrins. Physical Chemistry Chemical Physics 2012, 14 (46) , 15975. https://doi.org/10.1039/c2cp42957h
  35. Hayato Sakai, Mohammad Gulam Rabbani, Taku Hasobe. Porphyrin hexamer with a triphenylene core unit: Spectroscopy, electrochemistry and controllable supramolecular formation. Journal of Porphyrins and Phthalocyanines 2011, 15 (07n08) , 639-651. https://doi.org/10.1142/S1088424611003574
  36. Atsutoshi Yokoyama, Takahiko Kojima, Shunichi Fukuzumi. Enclosure of a Keggin-type heteropolyoxometalate into a tubular π-space via hydrogen bonds with a nonplanar Mo(v)-porphyrin complex forming a supramolecular assembly. Dalton Transactions 2011, 40 (24) , 6445. https://doi.org/10.1039/c0dt01708f
  37. Kazuo Tanaka, Takuya Matsumoto, Fumiyasu Ishiguro, Yoshiki Chujo. Conductivity regulation of the mixed-valence tetrathiafulvalene nanowire/poly(methyl methacrylate) composites using heterogeneous tetrathiafulvalene derivatives. Journal of Materials Chemistry 2011, 21 (26) , 9603. https://doi.org/10.1039/c1jm11161b
  38. Shunichi Fukuzumi. Artificial Photosynthetic Reaction Center. 2010,,, 111-132. https://doi.org/10.1007/978-90-481-2888-4_5
  39. . Structure and Function. 2010,,https://doi.org/10.1007/978-90-481-2888-4
  40. Taku Hasobe. Supramolecular nanoarchitectures for light energy conversion. Phys. Chem. Chem. Phys. 2010, 12 (1) , 44-57. https://doi.org/10.1039/B910564F
  41. Kazuo Tanaka, Fumiyasu Ishiguro, Tomoyuki Kunita, Yoshiki Chujo. Transparent conductive films based on polymer composites containing the mixed-valence tetrathiafulvalene nanofibers. Journal of Polymer Science Part A: Polymer Chemistry 2009, 47 (23) , 6441-6450. https://doi.org/10.1002/pola.23684
  42. Shunichi Fukuzumi, Tatsuhiko Honda, Kei Ohkubo, Takahiko Kojima. Charge separation in metallomacrocycle complexes linked with electron acceptors by axial coordination. Dalton Transactions 2009, 92 (20) , 3880. https://doi.org/10.1039/b901191a
  43. Tatsuhiko Honda, Takahiko Kojima, Shunichi Fukuzumi. Crystal structures and properties of a monoprotonated porphyrin. Chemical Communications 2009, 90 (33) , 4994. https://doi.org/10.1039/b910077f

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

OOPS

You have to login with your ACS ID befor you can login with your Mendeley account.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE