Bis-1,4-(p-diarylaminostryl)-2,5-dicyanobenzene Derivatives with Large Two-Photon Absorption Cross-Sections

Abstract

Synthesis and physical properties of novel multibranched two-photon materials are reported. The compound with three units of 4-(p-diphenylaminostyryl)-2,5-dicyanostyryl moieties attached to the central triphenylamine core exhibits a very large two-photon absorption cross-section.

Enhanced Two‐Photon Absorption of Organic Chromophores: Theoretical and Experimental Assessments

“…[33,36,57] In turn, exploitation of intermolecular interactions through branching strategies and the supramolecular approaches offers even more possibilities to tune or enhance TPA properties. This has already been demonstrated for branched chromophores built from the gathering of either dipolar [108][109][110][111][112][113][114][115][116][117][118][119][120][121][122][123] or quadrupolar [97,102,[124][125][126] sub-chromophores via common conjugated core moieties and multichromophore structures in which subchromophores interact only via electrostatic interactions. [127] Alternative routes such as those based on porphyrins, [128][129][130][131][132][133][134][135][136] oligomers and polymers [103,[137][138][139] have been explored as well.…”

“…A large body of experimental data is available for many families of quadrupolar systems. [3,33,36,57,58,63,76,78,81,85,86,[89][90][91][92][93][94][95][96][97][98][99][100][101][102][103][104][105][106][107] Their nonlinear response is a non-trivial function of terminal donor and acceptor strength, π-conjugated bridge length and type, nature of the conjugated core, torsional disorder, symmetry and topology. [58] In this subsection we exemplify some of these relationships using two different families of quadrupoles to derive general trends in terms of TPA cross sections and peak positions.…”

“…Thereby, attention has progressively moved from the well-known push-pull dipolar molecular structures [34,41,[75][76][77][78][79][80][81][82][83][84][85][86][87][88] to quadrupoles [3,33,36,57,58,63,76,78,81,85,86,[89][90][91][92][93][94][95][96][97][98][99][100][101][102][103][104][105][106][107] and, more recently, toward complex molecular architectures. Quadrupoles have been found to be more efficient than dipoles in terms of TPA, in particular for multiphoton-based opticallimiting applications.…”

Effects of (Multi)branching of Dipolar Chromophores on Photophysical Properties and Two-Photon Absorption

“…Lately, attention has turned toward multipolar [22][23][24][25][26][27][28][29][30][31][32][33] and branched structures including dendrimers. 23,24,28,[33][34][35][36][37][38][39][40][41][42][43] Given the huge synthetic effort needed to build such supramolecular structures, a detailed understanding of the effect of branching of molecular entities on the linear and nonlinear optical properties is of major interest. Thus, further development of approaches for rational design of NLO assemblies is needed in order to focus the synthesis on knowledgebased materials.…”

“…Triphenylamine is a well-known electrondonating moiety, which has been used both in the design of octupoles for second-order NLO effects [58][59][60][61] and in branched and dendritic structures for molecular TPA. [23][24][25][29][30][31][32][36][37][38]41,42 In this paper, we first briefly describe the synthesis of the studied chromophores, as well as experimental and computational details (section 2). Linear absorption and fluorescence properties of the compounds are then thoroughly explored through a combined analysis of both experimental and theoretical results (section 3).…”