Abstract
An antiaromatic compound 3,4,9,10-tetrahydrodicyclopenta[cd,lm] perylene, was synthesized by a coupling reaction. Its crystal structure was determined by X-ray diffraction. Crystal structures shows that the antiaromatic compounds are aggregated to J-aggregation materials. It further results ultrafast charge separation at organic interface and electron transfer in the aggregation materials. UV-vis spectrum shows that title compound has a broad UV-vis light absorbance at the wavelength range from 250 to 470 nm and a 2.67 eV energy gap value between the highest occupied and the lowest unoccupied molecular orbital energy levels.
Similar content being viewed by others
References
X. Y. Wang, A. Narita, X. L. Feng, et al., J. Am. Chem. Soc. 137, 7668 (2015).
Y. M. Sung, J. Oh, W. Kim, et al., J. Am. Chem. Soc. 137, 11856 (2015).
J. Zheng, X. H. Zhuang, L. Qiu, et al., J. Phys. Chem. A. 119, 3762 (2015).
A. Mahendran, P. Gopinath, and R. Breslow, Tetrahedron Lett. 56, 4833 (2015).
J. Zheng, X. H. Zhuang, L. Qiu, et al., J. Org. Chem. 80, 6679 (2015).
J. I. Wu, I. Fernández, and P. V. R. Schleyer, J. Am. Chem. Soc. 135, 315 (2013).
X. D. Xiong, C. L. Deng, X. S. Peng, et al., Org. Lett. 16, 3252 (2014).
P. Christos, G. A. Constantinides, A. A. Zissimou, et al., Org. Lett. 17, 4026 (2015).
J. Cao, G. London, O. Dumele, et al., J. Am. Chem. Soc. 137, 7178 (2015).
Q. Li, X. H. Zhang, N. Zhao, et al., Chem. Commun. 50, 3324 (2014).
G. Karthik, A. Srinivasan, C. H. Suresh, et al., Chem. Commun. 50, 12127 (2014).
Y. Ishimaru, N. Shimoyama, T. Fujihara, et al., Chem. Asian J. 10, 329 (2015).
S. Dai, Y. Lin, P. Cheng, et al., Dyes Pigm. 114, 283 (2015).
E. Kozma, D. Kotowski, M. Catellani, et al., Dyes. Pigm. 99, 329 (2013).
X. Zhang, Z. Lu, L. Ye, et al., Adv. Mater. 25, 5791 (2013).
X. Gong, M. Tong, F. G. Brunetti, et al., Adv. Mater. 23, 2272 (2011).
O. Y. Park, H. U. Kim, J.-H. Kim, et al., Energy Mater. Sol. Cells. 116, 275 (2013).
J. C. Hummelen, B. W. Knight, F. LePeq, et al., J. Org. Chem. 60, 532 (1995).
S. Verma and H. N. Ghosh. J. Phys. Chem. Lett. 3, 1877 (2012).
X. Qian and Y. Xiao, Tetrahedron Lett. 43, 2991 (2002).
A. R. Fotrester, H. Irikawa, R. H. Thomson, et al., J. Chem. Soc., Perkin Trans. 1: Org. Bio-Org. Chem. 6, 1712 (1981).
W. D. Neudorff, D. Lentz, M. Anibarro, et al., Chem. Eur. J. 2003 (9), 2745 (2003).
R. H. Mitchell, M. Chaudhary, R. V. Williams, et al., Can. J. Chem. 70, 1015 (1992).
J. Tatsugi, S. Okumura, and Y. Izawa, Bull. Chem. Soc. Jpn. 59, 3311 (1986).
CCDC1435826 (Crystallographic Data Centre, Cambridge). www.ccdc.cam.ac.uk/conts/retrieving.html.
G. M. Sheldrick, SADABS (Version 2.03). Program for Empirical Absorption Correction of Area Detector Data. (Univ. of Göttingen, Göttingen, 1996).
G. M. Sheldrick, SHELXS97. Program for the Solution of Crystal Structure (Univ. of Göttingen, Göttingen, 1997).
G. M. Sheldrick, SHELXL97. Program for the Refinement of Crystal Structure (Univ. of Göttingen, Göttingen, 1997).
Author information
Authors and Affiliations
Corresponding author
Additional information
The article is published in the original.
Rights and permissions
About this article
Cite this article
Li, T., Zhang, CZ., Su, YX. et al. Crystal structure and optoelectronic properties of antiaromatic compound 3,4,9,10-tetrahydrodicyclopenta[cd,lm]perylene. Crystallogr. Rep. 62, 885–888 (2017). https://doi.org/10.1134/S1063774517060165
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1063774517060165