Systematic Molecular Engineering of a Series of Aniline-Based Squaraine Dyes and Their Structure-Related Properties

Liu, Taihong; Liu, Xinglei; Wang, Weina; Luo, Zhipu; Liu, Muqiong; Zou, Shengli; Sissa, Cristina; Painelli, Anna; Zhang, Yuanwei; Vengris, Mikas; Bondar, Mykhailo V.; Hagan, David J.; Van Stryland, Eric W.; Fang, Yu; Belfield, Kevin D.

doi:10.1021/acs.jpcc.7b11997

Title: Systematic Molecular Engineering of a Series of Aniline-Based Squaraine Dyes and Their Structure-Related Properties

Journal Article · Thu Jan 25 00:00:00 EST 2018 · Journal of Physical Chemistry. C

DOI:https://doi.org/10.1021/acs.jpcc.7b11997· OSTI ID:1434732

^[1];

^[2]; Wang, Weina ^[3]; Luo, Zhipu ^[4]; Liu, Muqiong ^[5];

^[5]; Sissa, Cristina ^[6];

^[6];

^[2]; Vengris, Mikas ^[7]; Bondar, Mykhailo V. ^[8]; Hagan, David J. ^[5]; Van Stryland, Eric W. ^[5];

^[3];

^[1]

New Jersey Inst. of Technology, Newark, NJ (United States); Shaanxi Normal Univ., Xi’an (China)
New Jersey Inst. of Technology, Newark, NJ (United States)
Shaanxi Normal Univ., Xi’an (China)
Argonne National Lab. (ANL), Argonne, IL (United States)
Univ. of Central Florida, Orlando, FL (United States)
Univ. of Parma (Italy)
Light Conversion, Vilnius (Lithuania)
National Academy of Science of Ukraine (Ukraine)

With the objective of developing new near-infrared fluorescent probes and understanding the effect molecular structure exerts on physical properties, a series of aniline-based squaraine dyes with different number and position of methoxy substituents adjacent to the squaraine core were synthesized and investigated. Using both computational and experimental methods, we found that the subtle changes of the number or position of the methoxy substituents influenced the twisting angle of the structure and led to significant variations in optical properties. Moreover, the methoxy substituent also affected aggregation behavior due to steric effects. The X-ray crystal structure of one of the key members of the series, SD-2a, clearly demonstrates the distortion between the four-membered squaraine core and the adjacent aniline ring due to methoxy substitution. Structure-related fast relaxation processes were investigated by femtosecond pump–probe experiments and transient absorption spectra. Quantum chemical calculations and essential state models were exploited to analyze the primary experimental results. Here, the comprehensive investigation of structure-related properties of dihydroxylaniline-based squaraine dyes, with systematic substitution of OH by OCH₃ functional groups, serves as a guide for the design of novel squaraine dyes for photonics applications.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: National Science Foundation (NSF); U.S. National Academy of Sciences

Grant/Contract Number:: DMR-1609895; CBET-1517273; CHE-0832622; PGA-P210877

OSTI ID:: 1434732

Journal Information:: Journal of Physical Chemistry. C, Vol. 122, Issue 7; ISSN 1932-7447

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: ENGLISH

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Cited by: 22 works

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
dyes and pigments
reaction products
absorption
fluorescence
squaraine

Title: Systematic Molecular Engineering of a Series of Aniline-Based Squaraine Dyes and Their Structure-Related Properties

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