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Cyclopenta-fused perylene: a new soluble, stable and functionalizable rylene building block

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  • Chemistry
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Abstract

We report a facile synthesis of a [1,12-b,c,d]cyclopenta-fused perylene 5 from the parent perylene via a formylation-oxidative esterification–nucleophilic addition-followed-by-Friedel–Crafts alkylation strategy. Compared with the perylene, dye 5 exhibits much higher solubility, smaller energy gap, and can undergo regio-selective bromination at the peri-positions. Compared with the N-annulated perylene 8, compound 5 shows lower HOMO energy level and is more stable in air. Therefore, 5 can be regarded a new versatile building block for the development of high-order soluble and stable rylenes and various perylene-based functional materials.

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Acknowledgments

This work was supported by MOE Tier 2 Grant (MOE2011-T2-2-130), A*STAR-DST joint Grant (IMRE/14-2C0239) and A*STAR JCO Grant (1431AFG100).

Conflict of interest

The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Department of Chemistry, National University of Singapore, Singapore, 117543, Singapore

    Wangdong Zeng, Qingbiao Qi & Jishan Wu

  2. Institute of Materials Research and Engineering, A*STAR, Singapore, 117602, Singapore

    Jishan Wu

Authors
  1. Wangdong Zeng
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  2. Qingbiao Qi
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  3. Jishan Wu
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Correspondence to Jishan Wu.

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Zeng, W., Qi, Q. & Wu, J. Cyclopenta-fused perylene: a new soluble, stable and functionalizable rylene building block. Sci. Bull. 60, 1266–1271 (2015). https://doi.org/10.1007/s11434-015-0839-3

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  • DOI: https://doi.org/10.1007/s11434-015-0839-3

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