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

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

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

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. 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.

Original languageEnglish (US)
Pages (from-to)3994-4008
Number of pages15
JournalJournal of Physical Chemistry C
Volume122
Issue number7
DOIs
StatePublished - Feb 22 2018

Fingerprint

Aniline
aniline
Coloring Agents
Dyes
dyes
engineering
Substitution reactions
substitutes
probes
twisting
Relaxation processes
Photonics
Functional groups
Molecular structure
Absorption spectra
molecular structure
Agglomeration
Optical properties
Physical properties
physical properties

All Science Journal Classification (ASJC) codes

  • Electronic, Optical and Magnetic Materials
  • Energy(all)
  • Surfaces, Coatings and Films
  • Physical and Theoretical Chemistry

Cite this

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. / Systematic Molecular Engineering of a Series of Aniline-Based Squaraine Dyes and Their Structure-Related Properties. In: Journal of Physical Chemistry C. 2018 ; Vol. 122, No. 7. pp. 3994-4008.
@article{2ad897078742495ab1c73edfa9d8a69c,
title = "Systematic Molecular Engineering of a Series of Aniline-Based Squaraine Dyes and Their Structure-Related Properties",
abstract = "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. 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.",
author = "Taihong Liu and Xinglei Liu and Weina Wang and Zhipu Luo and Muqiong Liu and Shengli Zou and Cristina Sissa and Anna Painelli and Yuanwei Zhang and Mikas Vengris and Bondar, {Mykhailo V.} and Hagan, {David J.} and {Van Stryland}, {Eric W.} and Yu Fang and Kevin Belfield",
year = "2018",
month = "2",
day = "22",
doi = "https://doi.org/10.1021/acs.jpcc.7b11997",
language = "English (US)",
volume = "122",
pages = "3994--4008",
journal = "Journal of Physical Chemistry C",
issn = "1932-7447",
publisher = "American Chemical Society",
number = "7",

}

Liu, T, Liu, X, Wang, W, Luo, Z, Liu, M, Zou, S, Sissa, C, Painelli, A, Zhang, Y, Vengris, M, Bondar, MV, Hagan, DJ, Van Stryland, EW, Fang, Y & Belfield, K 2018, 'Systematic Molecular Engineering of a Series of Aniline-Based Squaraine Dyes and Their Structure-Related Properties', Journal of Physical Chemistry C, vol. 122, no. 7, pp. 3994-4008. https://doi.org/10.1021/acs.jpcc.7b11997

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.

In: Journal of Physical Chemistry C, Vol. 122, No. 7, 22.02.2018, p. 3994-4008.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Systematic Molecular Engineering of a Series of Aniline-Based Squaraine Dyes and Their Structure-Related Properties

AU - Liu, Taihong

AU - Liu, Xinglei

AU - Wang, Weina

AU - Luo, Zhipu

AU - Liu, Muqiong

AU - Zou, Shengli

AU - Sissa, Cristina

AU - Painelli, Anna

AU - Zhang, Yuanwei

AU - Vengris, Mikas

AU - Bondar, Mykhailo V.

AU - Hagan, David J.

AU - Van Stryland, Eric W.

AU - Fang, Yu

AU - Belfield, Kevin

PY - 2018/2/22

Y1 - 2018/2/22

N2 - 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. 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.

AB - 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. 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.

UR - http://www.scopus.com/inward/record.url?scp=85042536521&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85042536521&partnerID=8YFLogxK

U2 - https://doi.org/10.1021/acs.jpcc.7b11997

DO - https://doi.org/10.1021/acs.jpcc.7b11997

M3 - Article

VL - 122

SP - 3994

EP - 4008

JO - Journal of Physical Chemistry C

JF - Journal of Physical Chemistry C

SN - 1932-7447

IS - 7

ER -