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Synchrotron X-ray diffraction analysis
3. As pioneering examples: a) Aratani N, Osuka A,
KimYH, Jeong DH and Kim D. Angew. Chem., Int.
Ed. 2000; 39: 1458–1462. b) Tsuda A and Osuka A.
Science 2001; 293: 79–82.
4. a) Transition Metals in Supramolecular Chemistry,
Sauvage JP. (Ed.) John Wiley & Sons: Chichester,
1999. b) Metal-Containing and Metallosupramole-
cular Polymers and Materials, Schubert US, New-
kome GR and Manners I. (Eds.) ACS Symposium
Series 928: Washington DC, 2006.
High-resolution XRD analysis was carried out using a
synchrotron radiation X-ray beam with a wavelength of
1.00 Å on BL40B2 at SPring-8 (Hyogo, Japan). A large
Debye-Scherrer camera with a camera length of 532.7 mm
was used with an imaging plate as a detector, where the
diffraction pattern was obtained with a 0.01° step in 2q.
The exposure time to the X-ray beam was 10 s for 2n·ZnII
n
and 30 s for 2n·CuII and 2n·NiII sealed in a quartz capillary.
n
n
5. As representative book and review article: a) Falk
H. The Chemistry of Linear Oligopyrroles and Bile
Pigments, Springer-Verlag: Vienna, 1989. b) Wood
TE and Thompson A. Chem. Rev. 2007; 107: 1831–
1861. c) Baudron SA. CrystEngComm 2010; 12:
2288–2295.
6. Maeda H, Hasegawa M, Hashimoto T, Kakimoto T,
Nishio S and Nakanishi T. J. Am. Chem. Soc. 2006;
128: 10024–10025.
7. Meso–meso-linked BODIPY dimers: a) Cakmak
Y, Kolemen S, Duman S, Dede Y, Dolen Y, Kilic
B, Kostereli Z, Yildirim LT, Dogan AL, Guc D
and Akkaya EU. Angew. Chem., Int. Ed. 2011; 50:
11937–11941. b)Whited MT, Patel NM, Roberts ST,
Allen K, Djurovich PI, Bradforth SE and Thompson
ME. Chem. Commun. 2012; 48: 284–286.
SUMMARY
Novel dipyrrolyl ligand dimers were prepared. A
meso–meso directly linked dimer was found to form
metal-coordination polymers but was transformed into
a new p-conjugated system. Peripheral modification at
the pyrrole rings in these oligopyrrole derivatives would
result in the formation of functional metal-coordination
polymers, which could be useful as electrooptical
materials. In addition, the coordination with trivalent
metal cations would provide fascinating 2D honeycomb
coordination networks. Furthermore, metal-coordination
behaviors of ethene analogs 1 and 3, both of which
have two NH sites in the dipyrrolyl moieties, were also
observed during the preliminary examination. Further
detailed investigations are currently underway.
8. Other directly linked BODIPY dimers: a) Bröring
M, Bregier F, Kruger R and Kleeberg C. Eur. J.
Inorg. Chem. 2008; 5505–5512. b) Bröring M,
Kruger R, Link S, Kleeberg C, Kohler S, Xie X,
Ventura B and Flamigni L. Chem. Eur. J. 2008; 14:
2976–2983. c) Ventura B, Marconi G, Bröring M,
Kruger R and Flamigni L. New J. Chem. 2009; 33:
428–438. d) Rihn S, Erdem M, De Nicola A, Retail-
leau P and Ziessel R. Org. Lett. 2010; 12: 1916–
1919. e) Hayashi Y. Yamaguchi S, Cha WY, Kim D
and Shinokubo H. Org. Lett. 2010; 12: 2992–2995.
f) Nepomnyashchii AB, Bröring M, Ahrens J and
Bard AJ. J. Am. Chem. Soc. 2011; 133: 8633–8645.
9. a) Synthesis of dipyrrolylketone: Plater JP, Aiken S
and Bourhill G. Tetrahedron 2002; 58: 2405–2413.
b) Synthesis of tetrapyrrolylethene: Khoury RG,
Jaquinod L and Smith KM. Chem. Commun. 1997;
1057–1058.
Acknowledgements
This work was supported by Grant-in-Aid for
Scientific Research on Innovation Areas (“Coordination
Programming” Area 2107, No. 22108533) from the
MEXT and Ritsumeikan R-GIRO project (2008–2013).
We thank Prof. Atsuhiro Osuka and Mr. Tomohiro
Higashino, Kyoto University, for single-crystal X-ray
analysis, Dr. Takashi Nakanishi, NIMS, for SEM
measurements, Dr. Noboru Ohta, JASRI/SPring-8, for
synchrotron radiation XRD measurements (BL40B2 at
SPring-8), Prof. Toshiyuki Hamura, Kwansei Gakuin
University, for valuable discussion of electrocyclic
closing reaction, and Prof. Hitoshi Tamiaki, Ritsumeikan
University, for various measurements.
Supporting information
10. Gaussian 03 (Revision C.01), Frisch MJ, Trucks
GW, Schlegel HB, Scuseria GE, Robb MA, Chee-
seman JR, Montgomery JA Jr, Vreven T, Kudin
KN, Burant JC, Millam JM, Iyengar SS, Tomasi J,
Barone V, Mennucci B, Cossi M, Scalmani G, Rega
N, Petersson GA, Nakatsuji H, Hada M, Ehara M,
Toyota K, Fukuda R, Hasegawa J, Ishida M, Naka-
jima T, Honda Y, Kitao O, Nakai H, Klene M, Li X,
Knox JE, Hratchian HP, Cross JB, Adamo C, Jara-
millo J, Gomperts R, Stratmann RE,Yazyev O, Aus-
tin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala
PY, Morokuma K, Voth GA, Salvador P, Dannen-
berg JJ, Zakrzewski VG, Dapprich S, Daniels AD,
Figures S1–S7 are given in the supplementary material.
This material is available free of charge via the Internet at
REFERENCES
1. Supramolecular Chemistry from Molecules to
Nanomaterials, Gale PA and Steed JW. (Eds.)
Wiley: 2012.
2. Handbook of Porphyrin Science, Vol. 1–10, Kadish
KM, Smith KM and Guilard R. (Eds.) World Scien-
tific: New Jersey, 2010.
Copyright © 2013 World Scientific Publishing Company
J. Porphyrins Phthalocyanines 2013; 17: 90–91