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Croconaine Rotaxane Dye with 984 nm Absorption: Wavelength‐Selective Photothermal Heating
Author(s) -
McGarraugh Hannah H.,
Liu Wenqi,
Matthews Braden P.,
Smith Bradley D.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900082
Subject(s) - rotaxane , chemistry , absorption (acoustics) , photothermal therapy , photochemistry , absorption band , materials science , nanotechnology , molecule , optics , organic chemistry , supramolecular chemistry , physics , composite material
Croconaines are an emerging class of near‐infrared dyes that are useful for various sensing, photothermal, optoelectronic, and photoacoustic applications. Previous work encapsulated a dumbbell‐shaped croconaine dye whose structure contains two thiophene flanking units inside a tetralactam macrocycle and produced a croconaine rotaxane 1 with a narrow 824 nm absorption band. Herein, a new rotaxane 2 is reported that encapsulates a croconaine dye with two thienothiophene flanking units. The new croconaine rotaxane 2 exhibits a narrow 984 nm absorption band that is distinct from the 824 nm absorption of rotaxane 1 . Photothermal heating experiments showed that an 830 nm diode laser selectively heats a solution containing rotaxane 1 , with no heating of a solution containing rotaxane 2 . Conversely, a 980 nm diode laser selectively heats a solution containing rotaxane 2 , with no heating of a solution containing rotaxane 1 . The new croconaine rotaxane 2 shows no fatigue after four cycles of laser heating and cooling.