Synthesis, structure and use of functionalized naphthalenes

A method of synthesizing a fluorescent functionalized naphthalene comprising:

• reacting a 2′-alkynyl substituted halostyrene by a dehydrogenative intramolecular dehydro Diels Alder reaction in the presence of microwave irradiation to form a halo substituted naphthalene;
• and
• reacting the halo substituted naphthalene to a cross coupling reaction to form a functionalized naphthalene having a structure
• where R1 is a substituent selected from the group consisting of H, C1-C20 alkyl, C1-C20 alkoxy, phenyl, aryl, heteroaryl, —S(O)R4, —S(O)2R4, P(O)(OR4)2, and —C(Y)R4 where Y is O, NR5, or S;
• each R2 is a halogen or an electron donating group selected from —N(R6)2, —OR6, and —SR6;
• each R3 is H, C1-C20 alkyl, or combined as ═O;
• each R4, R5 and R6 is independently selected from H, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted phenyl, aryl, heteroaryl, benzyl, or may come together to form a cyclic structure;
• X is CH2, C(R6)2, C(CO2Alkyl)2, O, NTs, NH, NCOR5 or NR5;
• n is an integer from 0 to 2;
• m is an integer from 1 to 4,
• provided that either R1 is one of —S(O)R4, —S(O)2R4, P(O)(OR4)2, and —C(Y)R4 or the R3 groups are combined as ═O.