Reversible Solvatochromism of Polydiacetylenes Based on Extensively Hydrogen-Bonded Tubular Arrays
- Authors
- Kim, Bubsung; Heo, Jung-Moo; Khazi, Mohammed Iqbal; Kim, Jong-Man
- Issue Date
- Mar-2021
- Publisher
- AMER CHEMICAL SOC
- Citation
- MACROMOLECULES, v.54, no.5, pp.2485 - 2493
- Indexed
- SCIE
SCOPUS
- Journal Title
- MACROMOLECULES
- Volume
- 54
- Number
- 5
- Start Page
- 2485
- End Page
- 2493
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/1361
- DOI
- 10.1021/acs.macromol.1c00107
- ISSN
- 0024-9297
- Abstract
- Since the pioneering discovery by Wagner, polydiacetylenes (PDAs) and their solvatochromic properties (typically blue-to-red or purple transitions) have been the subject of extensive research efforts. Without exception, PDAs have been found to undergo irreversible solvent-induced color changes, and no cases exist in which initial blue states of the PDAs are regenerated after solvent removal. Herein, we describe the first example of a reversibly solvatochromic PDA that is derived from a macrocyclic diacetylene (MCDA) containing four carboxylic acid moieties. Infrared spectroscopic studies confirmed the synergetic interplay of intra- and intermolecular hydrogen-bonding interactions to control the reversibility. The weak intramolecular hydrogen bonds allowed a solvent-induced distortion of the PDA backbone (purple state) by releasing unpolymerized monomers, while the strong and networked intermolecular hydrogen-bonding interactions ensured the rigidity of the tubular channels and served as the driving forces for the recovery of the initial conformation (blue state).
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