Premium
Visible absorbing symmetrical squaraine and croconine dye derivatives: A comparative computational study
Author(s) -
Tripathi Anuj,
Prabhakar Chetti
Publication year - 2017
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3673
Subject(s) - chemistry , diradical , density functional theory , photochemistry , ring (chemistry) , molecule , absorption (acoustics) , acceptor , homo/lumo , red shift , visible spectrum , time dependent density functional theory , computational chemistry , organic chemistry , singlet state , physics , optoelectronics , quantum mechanics , galaxy , nuclear physics , acoustics , excited state , condensed matter physics
Visible absorbing C–N bonding squaraines (SQ1‐SQ5) and croconines (CR1‐CR5) with an increase in conjugation at donor groups and heteroaromatic donor substituents have been studied by density functional theory and time‐dependent density functional theory methodologies. In these molecules, croconines always have absorption nearly 100‐nm red shift than its corresponding squaraines (it is in consistent with C–C bonding, near infrared absorbing squaraine and croconines). The reason behind this drastic red shift, by changing the central acceptor of 4‐membered squarate ring with 5‐membered croconate ring, has been analyzed by considering the concept of diradical character and variation in central C–C–C angle. It is also observed that within the same series of molecules (either in squaraine or in croconines), with an increase in donor capacity (conjugation), absorption increases towards longer wavelength region because of destabilization of HOMO and stabilization of LUMO levels. A small blue shift was observed for heteroaromatic donor groups when compared with aromatic donor group.