## 3 Results and Discussion
### Spectroscopic Analysis on Charge-Transfer Complexes of Bar
\begin{table}
\begin{tabular}{c c c c c c} \hline
**CT Complex** & **M.Wt** & **E.Wt** & **Elemental** & **Infrared** & **1**HNMR** \\
**g/mol** & **F.Wt** & **Analysis \%** & **Assignments** & **Assignments** \\  & **g/mol** & & **(Calcd.)** & **cm\({}^{-1}\)** & **\& **(ppm)** \\ \hline  & & & & 1174; \(\
u_{\rm s}\)(C–N) & \\  & & & & 1270; \(\
u_{\rm s}\)(C–N) & \\  & & & N; 7.07 (7.12) & 1368 and 1456; \(\delta\)(C–H) & 11.37; (s, 2H, 2 NH) \\ (Bar–CLA) & 393.17 & C\({}_{14}\)H\({}_{14}\)Cl\({}_{2}\)N\({}_{2}\)O\({}_{7}\) & H; 3.50 (3.56) & 154; \(\
u\)(C=C) & 10.05; (s, 2H, 2 OH) \\  & & & C; 42.66 (42.73) & 1625; \(\delta\)(N–H) & 1.89; (q, 4H, 2 CH\({}_{2}\)) \\  & & & & 1674 and 1712; \(\
u_{\rm s}\)(C=O) & 0.81; (t, 6H, 2 CH\({}_{3}\)) \\  & & & & 1771; \(\
u_{\rm s}\)(C=O) & \\  & & & & 3220 and 3170; \(\
u\)(N–H) & \\ \hline  & & & & 1107; \(\
u_{\rm s}\)(C–N) & \\  & & & & 1320; \(\
u_{\rm s}\)(C–N) & \\  & & & N; 6.43 (6.51) & 1371 and 1439; \(\delta\)(C–H) & \\  & & & H; 2.84 (2.79) & 1460; \(\
u\)(C–C) & 11.92; (q, 4H, 2 CH\({}_{2}\)) \\  & & & C; 39.13 (39.07) & 1574; \(\delta\)(N–H) & \\  & & & & 1684; \(\
u_{\rm s}\)(C=O) & 0.83; (t, 6H, 2 CH\({}_{3}\)) \\  & & & & 1752; \(\
u_{\rm s}\)(C=O) & \\  & & & & 3160 and 3242; \(\
u\)(N–H) & \\ \hline  & & & & 1138; \(\
u_{\rm s}\)(C–N) & \\  & & & & 1321; \(\
u_{\rm s}\)(C–N) & \\  & & & & 1380 and 1468; \(\delta\)(C–H) & \\ (Bar–TCNQ) & 388.38 & C\({}_{20}\)H\({}_{16}\)N\({}_{6}\)O\({}_{3}\) & N; 21.70 (21.63) & 1521; \(\
u\)(C=C) & \\  & & & H; 4.08 (4.12) & 1675; \(\delta\)(N–H) & 7.72; (s, 4H, ArH) \\  & & & C; 61.75 (61.80) & 1714; \(\
u_{\rm s}\)(C=O) & 1.90; (q, 4H, 2 CH\({}_{2}\)) \\  & & & & 1763; \(\
u_{\rm s}\)(C=O) & 0.82; (t, 6H, 2 CH\({}_{3}\)) \\  & & & & 2223; \(\
u\)(C\(\equiv\)N) & \\  & & & & 3171 and 3209; \(\
u\)(N–H) & \\ \hline  & & & & 1157; \(\
u_{\rm s}\)(C–N) & \\  & & & & 1241; \(\
u_{\rm s}\)(C–N) & \\  & & & & 1380 and 1409; \(\delta\)(C–H) & \\  & & & N; 8.64 (8.69) & 1473; \(\
u\)(C–C) & \\  & & & H; 2.96 (2.90) & 1568; \(\
u\)(N–H) & \\  & & & C; 34.70 (34.74) & 1669; \(\delta\)(N–H) & \\  & & & & 1718; \(\
u_{\rm s}\)(C=O) & \\  & & & & 1767; \(\
u_{\rm s}\)(C=O) & \\  & & & & 3168 and 3256; \(\
u\)(N–H) & \\ \hline \end{tabular}
\end{table} 
Table 1: The spectroscopic characterization of all Barbital CT complexes. In the spectra of the four acceptors, the protons of (NH) groups were up-field shifted to 11.37, 11.17, 11.33, and 11.31 ppm for CLA, CHL, TCNQ and DBQ, respectively (Figure S2). It is possible that the complexation process is what caused these protons' up-field shift. Owing to the electronic clouds in the acceptors, all of the CT products that formed between Bar and the four acceptors had a shielding effect on the (NH) proton (Figure S2). The amount of shielding is dependent on the size of the electronic cloud and the electron-withdrawing the electron-donating properties of the acceptor. Compared to free Bar and other products, (Bar-TCNQ) demonstrated high thermal stability. TG thermogram results indicated that the four complexes were thermally stable up to 175, 200, 145, and 170 \({}^{\circ}\)C for (Bar-DBQ), (Bar-TCNQ), (Bar-CHL), and (Bar-CLA), respectively. It was observed that (Bar-TCNQ), (Bar-CHL), and (Bar-CLA) were thermally degraded in one step. Whereas, for (Bar-DBQ), the product diagram indicates that this product is thermally degraded in two steps in the temperature range of 175-315 and 315-600 \({}^{\circ}\)C.  
The determined particle diameters for (Bar-DBQ), (Bar-TCNQ), (Bar-CHL), and (Bar-CLA) were 48, 49, 70, and 56 nm, respectively. These results demonstrated the nanoscale nature of the products. The elemental compositions determined by EDX analyses and those determined by elemental analyses, as well as the suggested chemical composition of the products, are in good agreement. The products generally have a clear form, with homogenous and well-defined shape, according to SEM micrographs. Their particles have high homogeneity and resemblance and are evenly scattered.