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Polyladderane Constructed from a Gemini Monomer through Photoreaction
Author(s) -
Wang Zhihan,
Miller Benjamin,
Butz Jonathan,
Randazzo Katelyn,
Wang Zijun D.,
Chu Qianli R.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201705937
Subject(s) - monomer , chemistry , polymer , polymer chemistry , irradiation , photochemistry , materials science , crystallography , organic chemistry , physics , nuclear physics
Polyladderane, the first polymer to contain the ladderane functional group, was synthesized from a gemini monomer through photoreaction in the solid state. The modular design of the gemini monomers used to create polyladderane allowed specific structural modification, resulting in the formation of two distinct polymer products. Monomers were synthesized by connecting two photoreactive units, either sorbic acids (monomer I) or 2‐furanacrylic acids (monomer II), with a 1,4‐butanediol linker. Single‐crystal X‐ray diffraction analysis of the monomers confirmed that they packed in the desired head‐to‐tail orientation and within a viable distance for photoreaction by electronically complementary interaction. Pre‐organized gemini monomers were irradiated with UV light and monitored by FT‐IR. Two polyladderanes with cis , anti , cis ‐[3]‐ladderane as a characteristic functional group were constructed stereospecifically in 24–36 hours.