Cooperative proton‐electron transfer in a supramolecular structure of meso‐1,2‐bis‐(4‐dimethylaminophenyl)‐1,2‐ethanediol and bis(4‐cyanobenzylidene)ethylenediamine
Source abstract
Abstract
A supramolecular 1:1 complex of the title compounds undergoes light‐induced cooperative proton‐electron transfer which can be switched back by warming to 60°C. The complex (see Figure) is found to exhibit a unique from the photochromism, meaning that it could have potential in optical switching (with termal back switching) or optical data storage applications. magnified image
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Crystallography and molecular interactions · Photochromic and Fluorescence Chemistry · Photochemistry and Electron Transfer Studies
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (19)
Show source-provided references
1. 10.1007/BF0231018110.1007/BF02310181 ↗
2. C. A.Hunter Chem. Soc. Rev.1994 101.10.1039/cs9942300101 ↗
3. Foster R. · 1969
4. Soos Z. G. · 1975 · 1
5. 10.1002/047121374810.1002/0471213748 ↗
6. Bis(4‐cyanobenzylidene)ethylenediamine was prepared from 4‐cyanobenz‐aldehyde and ethylenediamine (ratio 2:1) in toluene at room temperature in the presence of molecular sieve 4 Å reaction time 12 h yield > 90% mp. 239°C. Anal Calc. for C18H14N4(286.29): C 75.50; H 4.93; N 19.57. Found: C 75.48;H 4.84; N 19.50.
7. 10.1016/S0040-4039(00)81521-X10.1016/S0040-4039(00)81521-X ↗
8. The UV/vis absorption spectrum was measured by preparing a transparent KBr pellet of the cocrystals and subtracting from its absorption spectrum that of a pure KBr pellet.
9. 1 kW Hanovia Hg/Xenon lamp with water and UG5 (Schott) filter.
10. We thank Dr.H.‐G.Korthfor the ESR measurement.
11. We thank Dr. Jonas Bayer AG Uerdingen for this measurement.
12. The data of a yellow and a black crystal (data in square brackets) of the compound with the dimensions ca. 0.55 × 0.22 × 0.17 [0.55 × 0.22 × 0.17]Å3were recorded with a Nicolet R3 m/V four circle diffractometer (MoKα‐radiation graphite‐monochromator) at 130 K [140 K]. Crystal System: triclinic cell dimensions: a = 6.157(2) [6.147(1)] Å b = 7.475(2) [7.469(2)] Å c = 16.893(5) [16.866(3)]Å α = 87.21(2) [87.54(3)]° β = 88.15(2) [87.89(3)]° γ = 87.71(2) [87.63(3)]° V = 775.5(4) [772.5(3)]Å3. Space group P1(No. 2) Z = 2. ρcal= 1.256 [1.261] g/cm3 μ = 0.08 mm−1 2θmax= 60 [55]° 3627 [3546] unique reflections (Rmerg= 0.0384 [0.0402]). The structure was solved using Direct Methods and refined on F2using SHELXL‐93.218 [225] parameters anisotropic displacement parameters for all non‐hydrogen atoms isotropic displacement parameters on all hydrogen atoms (idealized geometry for all H‐atoms except the hydroxyl‐hydrogen atoms). A disorder for the hydroxyl‐oxygen atoms was treated in the refinement with identical C–O distances and site occupation factors of 0.9 and 0.1 respectively. wR2= O. 1870 [0.1902] R1= 0.0714 [0.0737] for I > 2σ(I) w = 1/(σ2(F) + (aP)2+ b · P) with P = (max(0 F) + 2 F ·)/3 a = 0.1323 [0.1094] b = 0.29 [0.68] maximum residual electron density 0.45 [0.54] e/Å3. Supplementary material on the X‐ray structure determination may be obtained from the Cambridge Crystallographic Data Centre 12 Union Road Cambridge CB2 1 EZ (UK) on quoting the names of the authors and the journal citation.
13. 10.1021/ja00338a01110.1021/ja00338a011 ↗
14. Jaffé H. H. · 1962
15. Dürr H. · 1990
16. 10.1002/anie.19940181110.1002/anie.199401811 ↗
17. 10.1021/ja00005a07810.1021/ja00005a078 ↗
18. 10.1002/352760743910.1002/3527607439 ↗
19. Desiraju G. R. · Angew. Chem., Int. Ed. Engl. · 1995 · 34 · 232810.1002/anie.199523111 ↗