TY - JOUR
T1 - Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials
AU - Oliveira , Elisabete
AU - Baptista, Rosa M. F.
AU - Costa, Susana P. G.
AU - Raposo, M. Manuela M.
AU - Lodeiro, Carlos
N1 - Sem PDF
PY - 2014
Y1 - 2014
N2 - The demand for dyes with solvatochromic properties has increased in the last few years, mainly due totheir wide range of applications in the analytical and industrial fields, such as in the textile industry. Thephenomenon of solvatochromism is associated with the differential solvation of the ground and excitedstates of the solvatochromic compounds, leading to an important tool for the study of the natureof solute–solvent interactions. In this paper we report the synthesis of new bis(indolyl)methanederivatives bearing arylthiophene spacers (2a–d) functionalized with electron-donating and electronwithdrawinggroups, and the photophysical studies in different solvents, such as ethanol, acetonitrile,dichloromethane, trichloromethane, dimethylsulfoxide, diethylether and 1,4-dioxane. Aiming to exploretheir solvatochromic behaviour in the ground and excited states, all solvents employed have differenthydrogen-bond donor abilities. The largest colour modifications were visualized for compound 2b, thesolution colours of which are orange in DMSO, blue in trichloromethane, green in dichloromethane andpurple in 1,4-dioxane. A negative solvatochromism was observed in 2b and a positive one in 2a, 2c and 2d.
AB - The demand for dyes with solvatochromic properties has increased in the last few years, mainly due totheir wide range of applications in the analytical and industrial fields, such as in the textile industry. Thephenomenon of solvatochromism is associated with the differential solvation of the ground and excitedstates of the solvatochromic compounds, leading to an important tool for the study of the natureof solute–solvent interactions. In this paper we report the synthesis of new bis(indolyl)methanederivatives bearing arylthiophene spacers (2a–d) functionalized with electron-donating and electronwithdrawinggroups, and the photophysical studies in different solvents, such as ethanol, acetonitrile,dichloromethane, trichloromethane, dimethylsulfoxide, diethylether and 1,4-dioxane. Aiming to exploretheir solvatochromic behaviour in the ground and excited states, all solvents employed have differenthydrogen-bond donor abilities. The largest colour modifications were visualized for compound 2b, thesolution colours of which are orange in DMSO, blue in trichloromethane, green in dichloromethane andpurple in 1,4-dioxane. A negative solvatochromism was observed in 2b and a positive one in 2a, 2c and 2d.
KW - PHENOLATE BETAINE DYES
KW - STATE DIPOLE-MOMENTS
KW - LIQUID-CHROMATOGRAPHY
KW - SOLVENT POLARITIES
KW - POLYAMINES
KW - VALUES
KW - PHASE
KW - SCALE
KW - PH
U2 - 10.1039/c3pp50352f
DO - 10.1039/c3pp50352f
M3 - Article
C2 - 24317329
SN - 1474-905X
VL - 13
SP - 492
EP - 498
JO - Photochemical & Photobiological Sciences
JF - Photochemical & Photobiological Sciences
IS - 3
ER -