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Polymers Based on Benzodipyrrolidone and Naphthodipyrrolidone with Latent Hydrogen‐Bonding on the Main Chain
Author(s) -
Zhang Haichang,
Yang Kun,
Chen YuMing,
Bhatta Ram,
Tsige Mesfin,
Cheng Stephen Z. D.,
Zhu Yu
Publication year - 2017
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201600617
Subject(s) - stacking , hydrogen bond , polymer , coplanarity , conjugated system , side chain , polymer chemistry , molecule , hydrogen , chemistry , crystallography , materials science , organic chemistry , geometry , mathematics
A series of soluble π‐conjugated small molecules and polymers containing benzodipyrrolidone (BDP) or naphthodipyrrolidone (NDP) units with latent hydrogen‐bonding on the main chain is synthesized and characterized. Spectroscopic study confirms that the tert ‐butyloxycarbonyl ( t ‐Boc) side unit can be removed by facile thermal annealing treatment, generating the actual hydrogen‐bonded compounds. The resulting hydrogen‐bonded compounds exhibit distinctly different properties, for instance poorer solubility and smaller bandgap, as compared with their precursors with latent hydrogen‐bonding. The single crystal X‐ray structure analysis of t ‐Boc group substituted BDP and NDP indicates that the NDP compounds exhibit better coplanarity and a stronger π–π interaction. The density functional theory computation results of the polymer backbone segments show that the coplanarity of aromatic units is slightly improved. Such a hydrogen‐bonding‐mediated enhancement of π–π stacking exhibits potential for improving the performance of solution processable organic electronic materials. Hydrogen‐bonded polymer P‐NDP‐FL‐2 is an air stable n‐type semiconductor with electron mobility 40 times larger than its precursor polymer P‐NDP‐FL‐1 with latent hydrogen‐bonding.