Pyrroline Chromophores for Electro-Optics

Abstract

We have synthesized a new class of highly efficient nonlinear optical (NLO) chromophores based on the novel tricyanopyrroline (TCP) electron acceptor. Molecular linear and nonlinear optical properties of the prototypical chromophores were measured and calculated to understand structure-property relationships. One such chromophore showed molecular first hyperpolarizability (β) of (8700 ( 702) × 10 -30 esu at excitation wavelengths of 1.9 µm, and another showed macroscopic electro-optic (EO) coefficients (r 33 ) of 51 pm/V at 1.55 µm with 20 wt % chromophore loading when poled with 65 V/µm in amorphous polycarbonate film. Synthetic strategies for extending the utility of the acceptor and chromophores are discussed.

Electro-optic effect of a soluble nonlinear optical polyimide containing two different chromophores with different sizes in the side chain

“…10,11,[18][19][20] The precursor polyimide, PI-OH, 4 was also prepared by DOI 10.1007/s13233-011-0410-2 *Corresponding Author. E-mail: dhchoi8803@korea.ac.kr following the method in our previous work.…”

“…In order to design a highly active NLO chromophore, tricyanofuran (TCF)-and tricyanopyrroline (TCP)-based chromophores are employed; these are well known to have large permanent dipole moments and to exhibit electronic transitions at a higher wavelength. [8][9][10][11] Although the microscopic nonlinearity of a specific chromophore is relatively high, the macroscopic properties will be governed by the spatial arrangement of the chromophores in the polymer host. At a higher loading concentration, we normally observe a significant reduction in the EO effect due to chromophore aggregation, which is usually driven by strong intermolecular electrostatic interactions.…”

A tricyanopyrroline-based nonlinear optical chromophore bearing a lateral moiety: A novel steric technique for enhancing the electro-optic effect

“…Although the microscopic nonlinearity (mb(0)) of the planar and highly polar chromophore, 4a, is relatively high [12], the macroscopic nonlinearity in the polymer matrix cannot be high at a high loading level (>25%) into the host polymer. Thus, we have designed new chromophore structures for improving the poled alignment by reducing the dipoleedipole interaction in the polymer host.…”

“…Recently, very large microscopic nonlinearities were achieved by employing a tricyanopyrroline (TCP) acceptor to synthesize highly efficient planar NLO chromophores [12]. When the dipole moment of a chromophore is sufficiently high to align itself in an antiparallel manner, the planar chromophore molecules do not dissociate easily and get aligned even under a poling field.…”

Design and preparation of novel Diels–Alder crosslinking polymer and its application in NLO materials

“…Comparing with the traditional inorganic crystals and semiconductor nonlinear optical (NLO) materials, organic electro-optic (EO) polymers exhibit substantial advantages in the following aspects: fast response time, easy processing, low dielectric constant and ultra-large EO coefficients [1][2][3][4][5]. So, researchers have paid more and more attentions to organic EO materials in the past decades.…”