Research

”Back Cover” in New J. Chem., 42 (10), 8280 (2018)

”Cover Profile” in ChemPhysChem, 17 (11), 1543 (2016)

Boron-containing Nanoparticles

Boron Neutron Capture Therapy for Cancer

In 2020, p-boronophenylalanine (BPA) was approved for boron neutron capture therapy to treat head and neck tumors in Japan. Since BPA is not a perfect drug for the patients, we introduced nanoparticle-based boron drugs to improve their performance.

Selected Articles

M. Nishikawa,* J. Yu, H. G. Kang, M. Suzuki, N. Komatsu* "Rational Design, Multistep Synthesis and in Vitro Evaluation of　Poly(glycerol) Functionalized Nanodiamond Conjugated with　Boron-10 Cluster and Active Targeting Moiety for Boron Neutron　Capture Therapy" Chem. Eur. J., 2023, 29(63), e202302073 (11 pages) (DOI:10.1002/chem.202302073)
Y. Zhang, H. G. Kang, H. Xu, H. Luo, M. Suzuki, Q. Lan,* X. Chen,* N. Komatsu,* L. Zhao* "Tumor Eradication by Boron Neutron Capture Therapy with 10B-enriched Hexagonal Boron Nitride Nanoparticles Grafted with Poly(glycerol)" Adv. Mater., 2023, 35(35), 2301479 (12 pages) (DOI: 10.1002/adma.202301479).
Y. Wang, G. Reina, H. G. Kang, X. Chen, Y. Zou, Y. Ishikawa, M. Suzuki, N. Komatsu* "Polyglycerol Functionalized 10B Enriched Boron Carbide Nanoparticle as an Effective Bimodal Anticancer Nanosensitizer for Boron Neutron Capture and Photothermal Therapies" Small, 18(37), 2204044 (2022) (DOI:10.1002/smll.202204044).
M. Nishikawa,* H. G. Kang, Y. Zou, H. Takeuchi, N. Matsuno, M. Suzuki, N. Komatsu* "Conjugation of Phenylboronic Acid Moiety through Multistep Organic Transformations on Nanodiamond Surface for an Anticancer Nanodrug of Boron Neutron Capture Therapy" Bull. Chem. Soc. Jpn., 94(9), 2302-2312 (2021) [selected paper, highlighted at the inside cover, open access].

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Carbon Nanotubes

Structure-based Separation Utilizing Molecular Recognition

It is well-known that the physical properties of SWNTs are closely correlated to their structures. SWNTs with controlled structures are, therefore, in great demand both for fundamental studies and technological applications. SWNTs other than the armchair and zigzag types are intrinsically chiral. Although their optical properties have been predicted theoretically, optical activity originating solely from carbon nanotubes has not been reported so far. We have found optically active SWNTs for the first time by preferentially extracting either (M)- or (P)-stereoisomers with chiral porphyrin dimers.

Reviews

G. Liu, Y. Miyake, N. Komatsu* "Nanocalipers as novel molecular scaffolds for carbon nanotubes " Org. Chem. Front., 4 (5), 911-919 (2017).
N. Komatsu, "Interfance of nanocarbon: Activation and separation" C & I Commun., 42 (4), 21-23 (2017).
G. Liu, F. Wang, X. Peng, A. F. M. M. Rahman, A. K. Bauri, and N. Komatsu,* "Separation of Left- and Right-Handed Structures of Single-Walled Carbon Nanotubes through Molecular Recognition" Handbook of Biomedical Applications of Carbon Nanomaterials; K. M. Kadish and F. D'souza, Eds.; World Scientific: vol. 3, pp. 203-232 (2012).
N. Komatsu, "Sorting of Nanocarbon Materials (carbon nanotubes and nanodiamonds)", Powder Technology, 2 (11), 28-36 (2010).
X. Peng, F. Wang, A. F. M. M. Rahman, A. Bauri, and N. Komatsu,*"Optical Resolution of Single-Walled Carbon Nanotubes through Molecular Recognition with Chiral Diporphyrin Nanotweezers", Chem. Lett. (Highlight Review), 39 (10), 1022-1027 (2010).
N. Komatsu, and F. Wang, "A Comprehensive Review on Separation Methods and Techniques for Single-Walled Carbon Nanotubes", Materials (open access journal), 3 (7), 3818-3844 (2010).
N. Komatsu, "Novel and Practical Separation Processes for Fullerenes, Carbon Nanotubes and Nanodiamonds" J. Jpn. Petrol. Inst., 52 (3), 73-80 (2009).
N. Komatsu, "Sepaaration of Nanocarbons by Molecular Recognition", J. Incl. Phenom. Macrocycl. Chem., 61, 195-216 (2008) [highlighted at cover picture].
N. Komatsu, "Heterocyclic Supramolecular Chemistry of Fullerenes and Carbon Nanotubes" Topics in Heteroatom Chemistry; K. Matsumoto, Ed.; Springer: Heidelberg, Germany, pp 161-198 (2008).

Selected Articles

G. Cheng, T. Hayashi, Y. Miyake, T. Sato, H. Tabata, M. Katayama, N. Komatsu,* "Interlocking of Single-Walled Carbon Nanotubes with Metal-Tethered Tetragonal Nanobrackets to Enrich a Few Hundredths of a Nanometer Range in Their Diameters" ACS Nano, 16(8), 12500-12510 (2022) (DOI:10.1002/acsnano.2c03949).
A. Lopez Moreno,* Y. Jiang, G. Cheng, N. Komatsu* "Extraction of carbon nanotubes with porphyrin- and pyrene-based nanotweezers and nanocalipers: Insight from the association constants" J. Porphyrins Phthalocyanines, 24 (1-3), 314-319 (2020).
Y. Miyake, A. López-Moreno, J. Yang, H.-J. Xu, N. Desbois, C. P. Gros, N. Komatsu, "Synthesis of flexible nanotweezers with various metals and their application to carbon nanotube extraction" New J. Chem., 42(10), 7592-7594 (2018) [highlighted at the back cover].
G. Liu, F. Wang, S. Chunchaiyakul, Y. Saito, A. K. Bauri, T. Kimura, Y. Kuwahara, and N. Komatsu,* "Simultaneous Discrimination of Diameter, Handedness, and Metallicity of Single-Walled Carbon Nanotubes with Chiral Diporphyrin Nanocalipers", J. Am. Chem. Soc., 135 (12), 4805-4814 (2013) [highlighted in Chemical & Engineering News, 91 (12), p. 34, March 25, 2013].
A. F. M. M. Rahman, F. Wang, K. Matsuda, T. Kimura, and N. Komatsu,* "Diameter-based separation of single-walled carbon nanotubes through selective extraction with dipyrene nanotweezers" Chem. Sci., 2 (5), 862-867 (2011) [highlighted at the inside front cover].
F. Wang, K. Matsuda, A. F. M. M. Rahman, X. Peng, T. Kimura, and N. Komatsu,* "Simultaneous Discrimination of Handedness and Diameter of Single-Walled Carbon Nanotubes (SWNTs) with Chiral Diporphyrin Nanotweezers Leading to Enrichment of Single Enantiomer of (6,5)-SWNTs", J. Am. Chem. Soc., 132 (31), 10876-10881 (2010).
X. Peng, N. Komatsu,* T. Kimura, and A. Osuka, "Simultaneous Enrichments of Optical Purity and (n, m) Abundance of SWNTs through Extraction with 3,6-Carbazolylene-Bridged Chiral Diporphyrin Nanotweezers", ACS Nano, 2 (10), 2045-2050 (2008).
X. Peng, N. Komatsu,* T. Kimura, and A. Osuka, "Improved Optical Enrichment of SWNTs through Extraction with Chiral Nano-tweezers of 2,6-Pyridylene-bridged Diporphyrins", J. Am. Chem. Soc., 129 (51), 15947-15953 (2007).
X. Peng, N. Komatsu,* S. Bhattacharya, T. Shimawaki, S. Aonuma, T. Kimura, and A. Osuka, "Optically Active Single-Walled Carbon Nanotubes", Nature Nanotechnology, 2 (6), 361-365 (2007) [highlighted in Chemical & Engineering News (May 14, p. 41, 2007), Materials Today (10 (7-8), p. 13, 2007) and Kagaku (62 (7), p. 75, 2007)].

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Isolation of Ring-shaped Single-Walled Carbon Nanotubes Using Ultrasonic Atomization

Since the first observation of carbon nanotubes (CNTs) with transmission electron microscopy (TEM), it has been recognized that individual CNTs have a cylindrical shape and a strong propensity to form bundles. Also, CNT bundles are usually known to align in parallel or tangle to fabricate complex textures. However, other superstructures of CNTs, like rings and coils, attracted much attention due to their topologically interesting carbon structures at the curvatures and the potential for the characteristic properties especially in electromagnetic. In this context, we devised a very simple method for the isolation of circular single-walled carbon nanotubes by ultrasonic atomization, which has been utilized for concentration of alcohol, ketone and surfactant from their aqueous solutions. The sonoseparation process is applied for the first time to a solid-liquid heterogeneous system to obtain specific shape of the solid .

Reviews

N. Komatsu, "Toroidal Carbon Nanotubes Separated by Sonochemical Process", Journal of Japan Air Cleaning Association, 52 (1), 57 (2014).
N. Komatsu, "Ultrasound in nanocarbon chemistry", Ultrasonic Technology, 25 (1), 10-14 (2013).

Selected Articles

N. Komatsu, "Isolation of Ring-shaped Single-Walled Carbon Nanotubes Using Ultrasonic Atomization", Ultrasonic Technology, 19 (5), 63-66 (2007).
N. Komatsu,* T. Shimawaki, S. Aonuma and T. Kimura, "Ultrasonic Isolation of Toroidal Aggregates of Single-Walled Carbon Nanotubes" Carbon, 44 (10), 2091-2093 (2006).

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Nanodiamonds

Biomedical Application of Nanodiamonds and Nanoparticles

For in vivo applications of nanodiamonds and nanoprticles, they should be well dispersed in a physiological environment. We found that polyglycerol (PG) imparts enough aqueous dispersibility to various kinds of nanoparticles in a very facile process. PG coating also avoids protein corona formation and the subsequent macrophage uptake, giving good stealth efficiency. It also works as a scaffold for further chemical modification to give more functions to nanoparticles. Eventually, such functionalized nanoparticles are successfully applied to tumor imaging and therapy.

Reviews

N. Komatsu* "Poly(Glycerol)-Based Biomedical Nanodevices Constructed by Functional Programming on Inorganic Nanoparticles for Cancer Nanomedicine" Acc. Chem. Res., 56(2), 106-116 (2023) (DOI:10.1021/acs.accounts.2c00615).
Y. Zou, M. Nishikawa, N. Komatsu,* "Organic chemistry for nanodiamond: Controlled functionalization, quantitative characterization and structure-property relationship" Carbon Rep., 1(2), 70-78 (2022).
N. Komatsu, "Chemical Functionalization of Nanodiamond for Nanobiomedicine" Funtionalization of Nanocarbons; J.-C. Arnault and D. Eder, Eds.; Wiley: Chapter 7, pp 229-245 (2020).
G. Reina, L. Zhao, A. Bianco,* N. Komatsu,* "Chemical functionalization of nanodiamonds: opportunities and challenges ahead" Angew. Chem. Int. Ed., 58 (50), 17918-17929 (2019).
N. Komatsu, "Functionalized Carbon Nanomaterials for Drug Delivery" Carbon Nanomaterials for Bioimaging, Bioanalysis and Therapy; H.-C. Chang, Y. Y. Hui, H. Dong and X. Zhang, Eds.; Wiley: Chapter 10, pp 267-288 (2018).
N. Komatsu, L. Zhao, "Polyglycerol-Functionalized Nanoparticles for Biomedical Imaging" Carbon Nanoparticles and Nanostructures; N. Yang, X. Jiang, D.-W. Pang, Eds.; Springer: Chapter 5, pp. 139-159 (2016).
N. Komatsu, "Biomedical Applications of Fluorescence Nanodiamond", Optical and Electro-optical Engineering Contact, 54 (8), 12-19 (2016).
L. Zhao, and N. Komatsu,* "Surface Functionalization of Nanodiamond for Biomedical Applications: Polyglycerol Grafting and Further Derivatization", Chemical Functionalization of Carbon Nanomaterials: Chemistry and Applications; V. K. Thakur and M. K. Thakur, Eds.; CRC Press: Chapter 28, pp. 650-663 (2015).
N. Komatsu, "Application of Nanodiamond as Drug Carrier and Imaging Probe", New Diamond, 31 (2), 16-18 (2015).
N. Komatsu, "Sorting of Nanocarbon Materials (carbon nanotubes and nanodiamonds)", Powder Technology, 2 (11), 28-36 (2010).
T. Takimoto, Y. Morita, N. Kadota, S. Aonuma, T. Kimura, and N. Komatsu, "Surface Functionalization and Size Separation of Nanodiamond Aiming at Medicinal Applications", Chemical Engineering, 54 (12), 947-951 (2009).
N. Komatsu, "Medical Applications of Nanodiamonds", Function & Materials, 29 (6), 23-29 (2009).
N. Komatsu, "Size Separation and Surface Functionalization of Nanodiamond Particles Aiming at Their Biomedical Applications ", J. Surf. Sci. Jpn., 30 (5), 273-278 (2009).
N. Komatsu, "Novel and Practical Separation Processes for Fullerenes, Carbon Nanotubes and Nanodiamonds" J. Jpn. Petrol. Inst., 52 (3), 73-80 (2009).
N. Komatsu, "Separation of Nanocarbons by Molecular Recognition" J. Incl. Phenom. Macrocycl. Chem., 61, 195-216 (2008) [highlighted at cover picture].
N. Komatsu, "Diamond Technology", Diamond Industry Association Ed.; NGT Co., Chapter 9, 3-7 Medicinal Application of Diamonds, pp 683-687 (2007).
N. Komatsu, "Nanocarbon Science Aiming at Medicinal Applications", Chemical Engineering, 51 (12), 941-944 (2006).

Selected Articles

Y. Wang, G. Reina, H. G. Kang, X. Chen, Y. Zou, Y. Ishikawa, M. Suzuki, N. Komatsu* "Polyglycerol Functionalized 10B Enriched Boron Carbide Nanoparticle as an Effective Bimodal Anticancer Nanosensitizer for Boron Neutron Capture and Photothermal Therapies" Small, 18 (37), 2204044 (2022) (DOI:10.1002/smll.202204044).
Y. Zou, S. Ito, M. Fujiwara, N. Komatsu,* "Probing the role of charged functional groups on nanoparticles grafted with polyglycerol in protein adsorption and cellular uptake" Adv. Funct. Mater., 32(22), 2111077 (15 pages) (2022) [highlighted at the inside front cover].
M. Nishikawa,* H. G. Kang, Y. Zou, H. Takeuchi, N. Matsuno, M. Suzuki, N. Komatsu* "Conjugation of Phenylboronic Acid Moiety through Multistep Organic Transformations on Nanodiamond Surface for an Anticancer Nanodrug of Boron Neutron Capture Therapy" Bull. Chem. Soc. Jpn., 94(9), 2302-2312 (2021) [selected paper, highlighted at the inside cover, open access].
Y. Zou, M. Nishikawa, H. G. Kang, G. Cheng, W. Wang, Y. Wang, N. Komatsu,* "Effect of Protein Corona on Mitochondrial Targeting Ability and Cytotoxicity of Triphenylphosphonium Conjugated with Polyglycerol-Functionalized Nanodiamond" Mol. Pharmaceutics, 18(7), 2823-2832 (2021).
Y. Zou, S. Ito, F. Yoshino, Y. Suzuki, L. Zhao, N. Komatsu,* "Polyglycerol Grafting Shields Nanoparticle from Protein Corona Formation to Avoid Macrophage Uptake" ACS Nano, 14 (6), 7216-7226 (2020).
Y. Zou, N. Komatsu,* "Quantitative investigation of the interaction between proteins and charged functional groups on the polyglycerol-grafted nanodiamond surface" Carbon, 163, 395-401 (2020).
M. Fujiwara,* S. Sun, A. Dohms, Y. Nishimura, K. Suto, Y. Takezawa, K. Oshimi, L. Zhao, N. Sadzak, Y. Umehara, Y. Teki, N. Komatsu, O. Benson, Y. Shikano,* and E. Kage-Nakadai* "Real-time nanodiamond thermometry probingin-vivothermogenic responses" Sci. Adv., 6, eaba9636 (2020).
F. Yoshino, T. Amano, Y. Zou, J. Xu, F. Kimura, Y. Furusho, T. Chano, T. Murakami, L. Zhao,* N. Komatsu,* "Preferential tumor accumulation of polyglycerol functionalized nanodiamond conjugated with cyanine dye leading to near infrared fluorescence in vivo tumor imaging" Small, 15(48), 1901930 (2019). [highlighted at the back cover].
L. Zhao, Y.-H. Xu, H. Qin, S. Abe, T. Akasaka, T. Chano, F. Watari, T. Kimura, N. Komatsu,* and X. Chen* "Platinum on Nanodiamond: A Promising Prodrug Conjugated with Stealth Polyglycerol, Targeting Peptide, and Acid-Responsive Antitumor Drug" Adv. Funct. Mater., 24 (34), 5348-5357 (2014) [highlighted at the inside front cover].
L. Zhao, Y.-H. Xu, T. Akasaka, S. Abe, N. Komatsu, F. Watari, and X. Chen* "Polyglycerol-coated Nanodiamond as a macrophage-evading platform for selective drug delivery in cancer cells" Biomaterials, 35 (20), 5393-5406 (2014).
L. Zhao, T. Chano, S. Morikawa, Y. Saito, A. Shiino, S. Shimizu, T. Maeda, T. Irie, S. Aonuma, H. Okabe, T. Kimura, T.Inubushi, and N. Komatsu,* "Hyperbranched Polyglycerol-Grafted Superparamagnetic Iron Oxide Nanoparticles: Synthesis, Characterization, Functionalization, Size Separation, Magnetic Properties, and Biological Applications" Adv. Funct. Mater., 22 (24), 5107-5117 (2012).
L. Zhao, T. Takimoto, M. Ito, N. Kitagawa, T. Kimura, and N. Komatsu,* "Chromatographic Separation of Highly Soluble Diamond Nanoparticles Prepared by Polyglycerol Grafting" Angew. Chem. Int. Ed., 50 (6), 1388-1392 (2011) [highlighted at back cover].
T. Takimoto, T. Chano, S. Shimizu, H. Okabe, M. Ito, M. Morita, T. Kimura, T. Inubushi, and N. Komatsu,* “Preparation of Fluorescent Diamond Nanoparticles Stably Dispersed under a Physiological Environment through Multi-Step Organic Transformations”, Chem. Mater., 22 (11), 3462-3471 (2010).

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Graphene and 2D materials

Exfoliation of graphene and 2D materials

Graphene, hexagonal boron nitride (h-BN), molybdenum disulfide (MoS2), and tungsten disulfide (WS2) were exfoliated in water and organic solvents in the presence of exfoliant by use of sonication or ball milling. The graphene exfoliated with chlorin e6 (Ce6) was applied to cancer phototheraqpy.

Reviews

N. Komatsu, "BN for me (preface)" New Diamond, 35(2), 1-2 (2019).

Selected Articles

G. Liu,* P. Zhao, N. Liu, F. Yoshino, H. Qin, Y. Zou, S. Shi, T. Amano, J. R. Aguilar Cosme, Y. Nagano, H. Tamiaki, N. Komatsu* "Photosensitizer and anticancer drug-loaded 2D nanosheet: Preparation, stability and anticancer property" 2D Materials, 6(4), 045035 (2019).
A. Tayyebi, N. Ogino, T. Hayashi, N. Komatsu* "Size-controlled MoS2 nanosheet through ball milling exfoliation: parameter optimization, structural characterization and electrocatalytic application" Nanotechnology, 31(7), 075704 (2019).
G. Liu, N. Komatsu* "Readily available "stock solid" of MoS2 and WS2 nanosheets through solid phase exfoliation for highly concentrated dispersion in water" ChemNanoMat, ChemNanoMat, 2 (6), 500 - 503 (2016) [highlighted at the front cover and spotlights on our sister journals in Angew. Chem. Int. Ed., 35 (33), 9467 (2016)].
G. Liu, N. Komatsu* "An efficient and scalable production of 2D material dispersions using hexahydroxytriphenylene as a versatile exfoliant and dispersant" ChemPhysChem, 17 (11), 1557–1567 (2016) [highlighted at the front cover and the cover profile].
G. Liu, H. Qin, T. Amano, T. Murakami, and N. Komatsu,* "Direct Fabrication of the Graphene-Based Composite for Cancer Phototherapy through Graphite Exfoliation with a Photosensitizer" ACS Appl. Mater. Interfaces, 7 (42), 23402-23406 (2015).

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Fullerenes

Studies on an Interaction between Curved and Flat pai-Sufaces

We have investigated complex formation of fullerenes with flat pai-conjugated molecules of azulenes and porphyrins. Although they have unmatched shapes of the curved and flat surfaces, they showed very large binding constants of 103 - 105.
Although azulene is very small hydrocarbon consisting of only 10 carbons, it shows unexpectedly large binding constants to C60 and C70, which are larger than those of monoporphyrins and alternately conjugated aromatics. The energy-minimized structures reveal that the end-on structure of C70 is more stable than side-on, which may cause a similar affinity of azulene to C60 and C70.
Although there exists a number of examples of porphyrin-based hosts for fullerenes, we investigated complexation behavior of porphyrin monomers and dimers for fullerenes in solution. All the porphyrins show large binding constants in the range of 103 - 104 M-1 and 104 - 105 M-1 for KC60 and KC70, respectively.

Reviews

N. Komatsu, "Sepaaration of Nanocarbons by Molecular Recognition", J. Incl. Phenom. Macrocycl. Chem., 61, 195-216 (2008).
N. Komatsu, "Heterocyclic Supramolecular Chemistry of Fullerenes and Carbon Nanotubes" Topics in Heteroatom Chemistry; K. Matsumoto, Ed.; Springer: Heidelberg, Germany, pp 161-198 (2008).

Selected Articles

S. Bhattacharya,* M. Hashimoto, A. Fujimoto, T. Kimura, H. Uno, and N. Komatsu,"Photophysical properties of a novel Ni(II)-Diporphyrin in Presence of Fullerenes: Insights from Experimental and Theoretical Studies", Spectrochimica Acta A, 70 (2), 416-424 (2008).
S. Bhattacharya,* K. Tominaga, T. Kimura, H. Uno* and N. Komatsu* "A new metalloporphyrin dimer: effective and selective molecular tweezers for fullerenes" Chem. Phys. Lett., 433 (4-6), 395-402 (2007).
S. Bhattacharya,* N. Ujihashi, S. Aonuma, T. Kimura, and N. Komatsu,*"Spectral and theoretical studies on effective and selective non-covalent interaction between tetrahexylporphyrins and fullerenes" Spectrochimica Acta A, 68 (3), 495-503 (2007).
S. Bhattacharya,* T. Shimawaki, X. Peng, A. Ashokkumar, S. Aonuma, T. Kimura, and N. Komatsu,* "Spectroscopic and Theoritical Investigations on Effective and Selective Complexation between Porphyrins and Fullerenes" Chem. Phys. Lett., 430 (4-6), 435-442 (2006).
S. Bhattacharya,* N. Komatsu, M. Banerjee, "p-Electronic Charge-Transfer Interactions in Supramolecular Complex Formation between Fullerenes and 5,10,15,20-Tetrahexylporphyrin" Chem. Phys. Lett., 406 (4-6), 509-518 (2005).

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A Highly Improved Method for Purification of Fullerenes Applicable to Large-scale Production

There was a great demand for more efficient purification method exploitable for large-scale production of pure fullerenes. Such situation of fullerene production led the author to explore practical purification method of fullerenes. Eventually, we developed a very fast, facile and inexpensive method for the purification of C60 and C70 by passing a solution of fullerene extract through thin layer of activated carbon, which is promising for industrial-scale production .

Reviews

N. Komatsu, "Sepaaration of Nanocarbons by Molecular Recognition", J. Incl. Phenom. Macrocycl. Chem., 61, 195-216 (2008).
N. Komatsu, "Purification of Fullerenes", Petrotech, 26(5), 373-378(2003).

Selected Articles

N. Komatsu,* N. Kadota, T. Kimura, Y. Kikuchi and M. Arikawa "Remarkable Improvement in Efficiency of Filtration Method for Fullerene Purification" Fullerenes, Nanotubes and Carbon Nanostructures, 15 (4), 217-226 (2007).
N. Komatsu,* T. Ohe, and Kazumi Matsushige "A Highly Improved Method for Purification of Fullerenes Applicable to Large-scale Production" Carbon, 42, 163-167 (2004).

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Synthesis of Homooxacalix[n]arenas and Their Application to Separation of Fullerenes

In 1997, we found bismuth bromide-catalyzed reductive coupling reactions. The ether forming reactions proceeded under neutral conditions in the presence of a catalytic amount of bismuth bromide, which worked more efficiently than other catalysts reported so far. Since such mild conditions are favorable for constructing labile linkages such as dibenzyl ethers, we applied these reactions to the synthesis of macrocyclic molecules with dibenzyl ether linkages such as oxacyclophanes and oxacalixarenes.
Although it was already known that homooxacalix[3]arenes and their dimers form stable complexes with C60 in solutions, we obtained more attractive result that p-halohomooxacalix[3]arenes preferentially precipitate C70 from solutions.

Reviews

N. Komatsu, "Sepaaration of Nanocarbons by Molecular Recognition", J. Incl. Phenom. Macrocycl. Chem., 61, 195-216 (2008).

Selected Articles

N. Komatsu,* "Preferential Precipitation of C70 over C60 with p-Halohomooxacalix[3]arenes" Org. Biomol. Chem., 1(1), 204-209 (2003).
N. Komatsu,* "New Synthetic Route to Homooxacalix[n]arenes via Reductive Coupling of Diformylphenols" Tetrahedron Lett., 42(9), 1733-1736 (2001).
N. Komatsu,* and T. Chishiro, "Serial Synthesis of Oxa[3.n]cyclopanes and Homooxacalix[n]arenes via Reductive Coupling of Arenedialdehydes, and Their X-ray Structures" J. Chem. Soc., Perkin Trans. 1, (13), 1532-1537 (2001).

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