Here's why newer iPod/iPhone models will not charge in older (and some current) aftermarket boom boxes, radios and other accessories..
When Apple originally introduced the first iPod with a Dock Connector, they included two different charging specs. Pins #19 & #20 of the dock connector were reserved for +12 volt charging, which is the voltage from a Firewire port. Pin #23 of the dock connector was reserved for +5 volt charging, which is the voltage from a USB port.
The earliest dock connector iPods and the first iPhone supported BOTH Firewire and USB charging. But with the introduction of the iPhone 3G (and most of the iPod models introduced after the introduction of the iPhone 3G), Apple decided to drop support for Firewire charging. So, in those models, Pins #19 & #20 are not used. The only way to charge an iPhone and (most) iPods made since mid-2008 is via pin #23, which is USB +5 volt.
Unfortunately, MANY aftermarket manufacturers of boom boxes, radios, car adapters and other power accessories chose to go the Firewire +12 volt charging route to pin #19 or #20. That made particular good sense in the case of products for the car, because a car is already +12 volts. So, these products simply won't charge iPhones and (most) iPods made since mid-2008. And, sadly, some manufacturers CONTINUE to make products that charge via the Firewire pins.
Now, In the case of the iPod, I keep saying (most) because there is an exception. The iPod Classic still supports BOTH Firewire 12v and USB 5v charging. But it's the only iPod model that does.
For anyone interested, here is the pinout table for the dock connector:
http://pinouts.ru/PortableDevices/ipod_pinout.shtml
Mark