1：Experimental Design and Method Selection:

The study involved synthesizing two water-soluble calixarene scaffolds (compounds 1 and 2) and a conjugated polymer (poly-1) to investigate their fluorescence properties and response to NO gas. Methods included iodination, Ni-assisted arene homocoupling, sulfonation, Sonogashira cross-coupling, and oxidative polymerization. Fluorescence quenching experiments were conducted using NO gas bubbling and in situ NO generation from DEA NONOate (sodium 2-(N,N-diethylamino)-diazenolate).

2：Sample Selection and Data Sources:

Samples were synthesized compounds 1, 2, poly-1, and dye 12 (4-(4-(Dimethylamino)styryl)-N-Methylpyridinium). Solutions were prepared in degassed Millipore water or methanol at concentrations of 1-10 μM.

3：List of Experimental Equipment and Materials:

Equipment included NMR spectrometer, fluorescence spectrometer, and glove box for handling air-sensitive materials. Materials included calixarene precursors, catalysts (e.g., Ni(COD)2, Pd2(dba)3), solvents (e.g., DMF, DMSO, MeOH, H2O), and NO sources (NO gas, DEA NONOate).

4：Experimental Procedures and Operational Workflow:

Synthesis involved multiple steps as per Schemes 1-3. For NO detection, solutions were treated with NO gas or DEA NONOate, stirred, and fluorescence spectra were recorded over time. Control experiments with other gases (CO2, O2, NO2) were performed.

5：For NO detection, solutions were treated with NO gas or DEA NONOate, stirred, and fluorescence spectra were recorded over time. Control experiments with other gases (CO2, O2, NO2) were performed. Data Analysis Methods:

5. Data Analysis Methods: Fluorescence quenching was analyzed using emission spectra. Binding constants were calculated using fitting software. Quantum yields and Stern-Volmer constants were determined.